DD146599A5 - Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid - Google Patents

Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid Download PDF

Info

Publication number: DD146599A5
Authority: DD; German Democratic Republic
Prior art keywords: oxathiolane; phenyl; methyl; solvent; item
Prior art date: 1978-09-05

Application number

DD79215367A

Other languages

German (de)

English (en)

Inventor

Andrew A Znotins

Arthur D Brewer

Original Assignee

Uniroyal Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-09-05

Filing date

1979-09-05

Publication date

1981-02-18

1979-09-05 Application filed by Uniroyal Ltd filed Critical Uniroyal Ltd

1981-02-18 Publication of DD146599A5 publication Critical patent/DD146599A5/de

Links

GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title 1
239000002904 solvent Substances 0.000 claims abstract description 48
238000000034 method Methods 0.000 claims abstract description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims abstract description 30
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims abstract description 26
OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims abstract description 26
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims abstract description 20
230000008569 process Effects 0.000 claims abstract description 18
239000003960 organic solvent Substances 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 12
-1 2-methyl-N-phenyl-1 Chemical compound 0.000 claims abstract description 11
125000005907 alkyl ester group Chemical group 0.000 claims abstract description 11
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 11
230000003197 catalytic effect Effects 0.000 claims abstract description 10
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 10
238000010438 heat treatment Methods 0.000 claims abstract description 9
150000002736 metal compounds Chemical class 0.000 claims abstract description 8
238000006049 ring expansion reaction Methods 0.000 claims abstract description 7
230000002378 acidificating effect Effects 0.000 claims abstract description 6
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims abstract description 5
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 95
238000006243 chemical reaction Methods 0.000 claims description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
KKUZZLRZTGQZQO-UHFFFAOYSA-N 2-(2-methyl-3-oxo-1,3-oxathiolan-2-yl)-n-phenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1(C)OCCS1=O KKUZZLRZTGQZQO-UHFFFAOYSA-N 0.000 claims description 20
238000009835 boiling Methods 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 17
239000011541 reaction mixture Substances 0.000 claims description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
238000007254 oxidation reaction Methods 0.000 claims description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
230000003647 oxidation Effects 0.000 claims description 11
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 10
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
239000012074 organic phase Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
230000008859 change Effects 0.000 claims description 5
229910001385 heavy metal Inorganic materials 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000006482 condensation reaction Methods 0.000 claims description 4
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 4
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 claims description 4
NQIICSBSMAOADW-UHFFFAOYSA-N 2-(2-methyl-1,3-oxathiolan-2-yl)-n-phenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1(C)OCCS1 NQIICSBSMAOADW-UHFFFAOYSA-N 0.000 claims description 3
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical class O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 claims description 3
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 3
GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 claims description 3
NHVQEBNAVLTNPT-UHFFFAOYSA-N 2-phenyl-1,4-oxathiine-3-carboxamide Chemical compound C1(=CC=CC=C1)C=1OC=CSC=1C(=O)N NHVQEBNAVLTNPT-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
229940011051 isopropyl acetate Drugs 0.000 claims description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 2
229910052721 tungsten Inorganic materials 0.000 claims description 2
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
150000003754 zirconium Chemical class 0.000 claims description 2
238000000151 deposition Methods 0.000 claims 3
230000008021 deposition Effects 0.000 claims 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 1
JNGOMLQBEBRITP-UHFFFAOYSA-N 3,3,3-triphenylpropylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC[PH3+])C1=CC=CC=C1 JNGOMLQBEBRITP-UHFFFAOYSA-N 0.000 claims 1
ATLHLWUMBUBUPU-UHFFFAOYSA-N 3-phenylpropylphosphanium;bromide Chemical compound [Br-].[PH3+]CCCC1=CC=CC=C1 ATLHLWUMBUBUPU-UHFFFAOYSA-N 0.000 claims 1
GKJMGRNQNUBUMM-UHFFFAOYSA-N 5-(3-methylphenyl)-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CC1=CC=CC(C=2NNC(=S)N=2)=C1 GKJMGRNQNUBUMM-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
229940107816 ammonium iodide Drugs 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 1
239000010937 tungsten Substances 0.000 claims 1
YGHWXJJKYJXSAY-UHFFFAOYSA-N oxathiolane 2-oxide Chemical compound O=S1CCCO1 YGHWXJJKYJXSAY-UHFFFAOYSA-N 0.000 abstract description 18
150000004010 onium ions Chemical class 0.000 abstract description 9
125000001931 aliphatic group Chemical group 0.000 abstract description 5
125000005537 sulfoxonium group Chemical group 0.000 abstract description 3
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
239000003899 bactericide agent Substances 0.000 abstract description 2
230000000855 fungicidal effect Effects 0.000 abstract description 2
150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
239000000725 suspension Substances 0.000 abstract description 2
VQUUZIGLUMWMSD-UHFFFAOYSA-N azete-2-carboxamide Chemical compound NC(=O)C1=NC=C1 VQUUZIGLUMWMSD-UHFFFAOYSA-N 0.000 abstract 1
239000000417 fungicide Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000376 reactant Substances 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
JZOFKEVYAHEKJC-UHFFFAOYSA-N N-phenyl-2,5-diazabicyclo[2.2.0]hexa-1(4),2,5-triene-3-carboxamide Chemical compound N1=C(C2=C1C=N2)C(=O)NC1=CC=CC=C1 JZOFKEVYAHEKJC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000004280 Sodium formate Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
235000019254 sodium formate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
FBLZDUAOBOMSNZ-UHFFFAOYSA-M tetrapentylazanium;iodide Chemical compound [I-].CCCCC[N+](CCCCC)(CCCCC)CCCCC FBLZDUAOBOMSNZ-UHFFFAOYSA-M 0.000 description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
XQSPYNMVSIKCOC-RITPCOANSA-N 4-amino-5-fluoro-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)SC1 XQSPYNMVSIKCOC-RITPCOANSA-N 0.000 description 1
STWQTDHSLQGNMB-UHFFFAOYSA-N 6-methyl-n-(2-methylphenyl)-2,3-dihydro-1,4-oxathiine-5-carboxamide Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1C STWQTDHSLQGNMB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
PWSLEYKRGZRWEQ-UHFFFAOYSA-O CC1[S+](CC(NC2=CC=CC=C2)=O)CCO1 Chemical compound CC1[S+](CC(NC2=CC=CC=C2)=O)CCO1 PWSLEYKRGZRWEQ-UHFFFAOYSA-O 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
LQEJKDNALLXRCT-UHFFFAOYSA-N chloroform;toluene Chemical compound ClC(Cl)Cl.CC1=CC=CC=C1 LQEJKDNALLXRCT-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
210000003746 feather Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009941 weaving Methods 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
150000003755 zirconium compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

DD79215367A 1978-09-05 1979-09-05 Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid DD146599A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA310,606A CA1109073A (fr)	1978-09-05	1978-09-05	Methode de preparation de la 5,6-dihydro-2-methyl-n- phenyl-1,4-oxathiine-3-carboxamide

Publications (1)

Publication Number	Publication Date
DD146599A5 true DD146599A5 (de)	1981-02-18

Family

ID=4112287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215367A DD146599A5 (de)	1978-09-05	1979-09-05	Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid

Country Status (12)

Country	Link
EP (2)	EP0010843B1 (fr)
JP (3)	JPS5535099A (fr)
AU (1)	AU526670B2 (fr)
CA (1)	CA1109073A (fr)
CS (2)	CS215124B2 (fr)
DD (1)	DD146599A5 (fr)
DE (1)	DE2966391D1 (fr)
HU (1)	HU182614B (fr)
PL (1)	PL124628B1 (fr)
SU (1)	SU1029828A3 (fr)
YU (1)	YU216479A (fr)
ZA (1)	ZA794694B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5811812A (ja) *	1981-07-16	1983-01-22	Yokogawa Hokushin Electric Corp	メモリ一式のレコ−ダ
AU637370B2 (en) *	1989-05-18	1993-05-27	Fujikura Ltd.	Ptc thermistor and manufacturing method for the same
CN111253289A (zh) *	2020-03-27	2020-06-09	湖南吴赣药业有限公司	一种磺胺醋酰钠的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1036167A (fr) *	1977-05-06	1978-08-08	Wha S. Lee	Procede de preparation de derives de dihydro-5,6 methyl-2 oxathiine-1,4
CA1035778A (fr) *	1977-05-06	1978-08-01	Wha S. Lee	Mode de preparation de derives de 5,6-dihydro-2-methyl-1,4 oxathiine

1978
- 1978-09-05 CA CA310,606A patent/CA1109073A/fr not_active Expired
1979
- 1979-09-04 HU HU79UI283A patent/HU182614B/hu not_active IP Right Cessation
- 1979-09-05 PL PL1979218135A patent/PL124628B1/pl unknown
- 1979-09-05 SU SU792806608A patent/SU1029828A3/ru active
- 1979-09-05 ZA ZA00794694A patent/ZA794694B/xx unknown
- 1979-09-05 DD DD79215367A patent/DD146599A5/de unknown
- 1979-09-05 JP JP11403879A patent/JPS5535099A/ja active Granted
- 1979-09-05 EP EP79301827A patent/EP0010843B1/fr not_active Expired
- 1979-09-05 EP EP81106224A patent/EP0042182A3/fr not_active Withdrawn
- 1979-09-05 CS CS81458A patent/CS215124B2/cs unknown
- 1979-09-05 CS CS796017A patent/CS215123B2/cs unknown
- 1979-09-05 AU AU50603/79A patent/AU526670B2/en not_active Ceased
- 1979-09-05 YU YU02164/79A patent/YU216479A/xx unknown
- 1979-09-05 DE DE7979301827T patent/DE2966391D1/de not_active Expired
1980
- 1980-11-27 JP JP16733780A patent/JPS5699470A/ja active Pending
- 1980-11-27 JP JP16733680A patent/JPS5699469A/ja active Pending

Also Published As

Publication number	Publication date
AU526670B2 (en)	1983-01-27
EP0010843B1 (fr)	1983-11-09
EP0042182A2 (fr)	1981-12-23
PL218135A1 (fr)	1980-07-01
CS215124B2 (en)	1982-07-30
EP0042182A3 (fr)	1981-12-30
AU5060379A (en)	1980-04-17
JPS5623989B2 (fr)	1981-06-03
DE2966391D1 (en)	1983-12-15
JPS5699469A (en)	1981-08-10
CS215123B2 (en)	1982-07-30
JPS5699470A (en)	1981-08-10
PL124628B1 (en)	1983-02-28
YU216479A (en)	1983-02-28
JPS5535099A (en)	1980-03-11
HU182614B (en)	1984-02-28
EP0010843A1 (fr)	1980-05-14
CA1109073A (fr)	1981-09-15
ZA794694B (en)	1980-08-27
SU1029828A3 (ru)	1983-07-15

Publication	Publication Date	Title
EP0215347B1 (fr)	1990-01-24	Procédé pour la préparation de 6-méthyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxyde ainsi que pour sa purification
EP0025843B1 (fr)	1985-06-19	Préparation de monoéthers alcoyles d'hydroxyphénols et leur transformation en hydroxycoumaranes
EP0011091B1 (fr)	1981-07-15	Procédé de préparation d'alcoyl- ou d'arylthiométhyl-phénols
CH661268A5 (de)	1987-07-15	Verfahren zur herstellung von arylalkansaeureestern und deren umwandlung in arylalkancarbonsaeuren.
DD146599A5 (de)	1981-02-18	Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid
DE4317322A1 (de)	1994-12-01	Verfahren zur Herstellung von Difluormethoxy- und Difluormethylhioarenen
WO2005075401A1 (fr)	2005-08-18	Procede pour produire de l'acide 2,5-dimethylphenylacetique
EP0498847B1 (fr)	1994-09-14	Procede de preparation de 1,4-bis-(4-hydroxybenzoyl)-benzol
DE10026750A1 (de)	2001-01-18	Verfahren zur Herstellung von Retinin und Zwischenprodukte zur Herstellung desselben
DE2609015A1 (de)	1976-09-16	Verfahren zur herstellung von benz (f)-2,5-oxazocinen
DE3814781A1 (de)	1989-11-09	Verfahren zur herstellung von 2-hydroxy-4-(2'-hydroxyethoxy)-benzophenonen
EP0401626B1 (fr)	1994-01-19	Procédé pour la préparation d'éther diphényl chloré
EP0019112B1 (fr)	1982-11-17	Procédé pour la préparation d'acétals cycliques de trans-4-chloro-3-méthyl-2-butén-1-al et préparation de trans-3-méthyl-2-butén-1,4-dial-monoacétals
EP0035635B1 (fr)	1983-10-19	Procédé de préparation de triméthylbenzoquinone
DE2944030A1 (de)	1980-05-08	Verfahren zur herstellung von aminophenolaether
DE4408083C1 (de)	1995-01-26	Verfahren zur Herstellung von 4-Fluoralkoxyzimtsäurenitrilen
EP0573999A1 (fr)	1993-12-15	Procédé pour la préparation d'esters tétroniques
EP0157225B1 (fr)	1988-01-20	Procédé pour la préparation de dérivés de l'acide benzimidazolyl, benzoxazolyl et benzothiazolyloxyphénoxypropionique
DE68915904T2 (de)	1994-11-17	Verfahren zur Herstellung von Para-bromphenoxyacetaldehyd-dialkylacetal-Derivaten.
DE3622533A1 (de)	1988-01-07	Verfahren zur herstellung von perfluoralkylalkenolen
CH656610A5 (de)	1986-07-15	Verfahren zur herstellung von 2-cyclopentenonen.
DE2657477C2 (de)	1985-01-24	Verfahren zur Herstellung von Canthaxanthin
DE3307164A1 (de)	1983-09-08	Verfahren zur herstellung von nitrophenetolen
DE2854152A1 (de)	1980-02-07	Verfahren zur herstellung von anilinderivaten
EP0212608A1 (fr)	1987-03-04	Procédé pour la préparation de sulfures d'halogénophényle et d'hydroxyéthyle et de leurs produits d'oxydation