DD202022A5 - Verfahren zur sulfenylierung von n-alkylcarbamaten - Google Patents

Verfahren zur sulfenylierung von n-alkylcarbamaten Download PDF

Info

Publication number: DD202022A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; item; triethylamine; carbamate; solvent
Prior art date: 1980-10-31

Application number

DD81234496A

Other languages

German (de)

English (en)

Inventor

John W Ager

Maurice J Harding

Charles E Ihatch

Original Assignee

Fmc Corp

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.)

1980-10-31

Filing date

1981-10-30

Publication date

1983-08-24

1981-10-30 Application filed by Fmc Corp filed Critical Fmc Corp

1983-08-24 Publication of DD202022A5 publication Critical patent/DD202022A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 41
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims abstract description 32
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 74
-1 sulfenyl halide Chemical class 0.000 claims abstract description 36
239000002904 solvent Substances 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 26
230000003197 catalytic effect Effects 0.000 claims abstract description 8
238000005991 sulfenylation reaction Methods 0.000 claims abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 141
125000004432 carbon atom Chemical group C* 0.000 claims description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
125000005270 trialkylamine group Chemical group 0.000 claims description 14
150000003461 sulfonyl halides Chemical class 0.000 claims description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 8
238000011065 in-situ storage Methods 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 46
238000002360 preparation method Methods 0.000 abstract description 21
150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 8
150000003973 alkyl amines Chemical class 0.000 abstract description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 82
239000000203 mixture Substances 0.000 description 29
239000000370 acceptor Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
125000000217 alkyl group Chemical group 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000010410 layer Substances 0.000 description 13
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
239000000047 product Substances 0.000 description 10
BKFZQRHTZYGWPW-UHFFFAOYSA-N (dibutylamino) thiohypochlorite Chemical compound CCCCN(SCl)CCCC BKFZQRHTZYGWPW-UHFFFAOYSA-N 0.000 description 9
FABFUHUAVHHSSM-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) n-[(dibutylamino)sulfanylmethyl]carbamate Chemical compound CCCCN(CCCC)SCNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 FABFUHUAVHHSSM-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
238000002955 isolation Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
239000012433 hydrogen halide Substances 0.000 description 4
229910000039 hydrogen halide Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
230000006103 sulfonylation Effects 0.000 description 4
238000005694 sulfonylation reaction Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
PAJQNXUWYZXFIX-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)disulfanyl]butan-1-amine Chemical compound CCCCN(CCCC)SSN(CCCC)CCCC PAJQNXUWYZXFIX-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
125000004953 trihalomethyl group Chemical group 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
125000003282 alkyl amino group Chemical group 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
229910052794 bromium Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
JMKNHDJWTWEEHO-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) n-(morpholin-4-ylsulfanylmethyl)carbamate Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC(=O)NCSN1CCOCC1 JMKNHDJWTWEEHO-UHFFFAOYSA-N 0.000 description 1
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SZCYUFPFQGHOMZ-UHFFFAOYSA-N 2,2-dimethyl-3h-cyclopenta[b]pyran Chemical compound O1C(C)(C)CC=C2C=CC=C21 SZCYUFPFQGHOMZ-UHFFFAOYSA-N 0.000 description 1
FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 1
125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000005916 Methomyl Substances 0.000 description 1
GDIHDSKOVXEJQQ-UHFFFAOYSA-N NC(O)=O.NC(O)=O.NC(O)=O.N Chemical compound NC(O)=O.NC(O)=O.NC(O)=O.N GDIHDSKOVXEJQQ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
QGLZXHRNAYXIBU-UHFFFAOYSA-N aldicarb Chemical compound CNC(=O)ON=CC(C)(C)SC QGLZXHRNAYXIBU-UHFFFAOYSA-N 0.000 description 1
QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
ZBVZOMFYISPWMD-UHFFFAOYSA-N amino thiohypochlorite Chemical class NSCl ZBVZOMFYISPWMD-UHFFFAOYSA-N 0.000 description 1
OGRKVXBDXAVTBV-UHFFFAOYSA-N aminosulfanylcarbamic acid Chemical compound NSNC(O)=O OGRKVXBDXAVTBV-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
125000004276 dioxalanyl group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
KWTCAZADHRCBIP-UHFFFAOYSA-N morpholin-4-yl thiohypochlorite Chemical compound ClSN1CCOCC1 KWTCAZADHRCBIP-UHFFFAOYSA-N 0.000 description 1
LVBMTUWLSHSMOA-UHFFFAOYSA-N naphthalen-1-yl n-[(dibutylamino)sulfanylmethyl]carbamate Chemical compound C1=CC=C2C(OC(=O)NCSN(CCCC)CCCC)=CC=CC2=C1 LVBMTUWLSHSMOA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000010791 quenching Methods 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000019635 sulfation Effects 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7

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)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Furan Compounds (AREA)

DD81234496A 1980-10-31 1981-10-30 Verfahren zur sulfenylierung von n-alkylcarbamaten DD202022A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/202,526 US4329293A (en)	1980-10-31	1980-10-31	Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates

Publications (1)

Publication Number	Publication Date
DD202022A5 true DD202022A5 (de)	1983-08-24

Family

ID=22750253

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81234496A DD202022A5 (de)	1980-10-31	1981-10-30	Verfahren zur sulfenylierung von n-alkylcarbamaten

Country Status (11)

Country	Link
US (1)	US4329293A (fr)
EP (1)	EP0051273B1 (fr)
JP (2)	JPS5941990B2 (fr)
KR (1)	KR850000926B1 (fr)
BR (1)	BR8106825A (fr)
CA (1)	CA1173053A (fr)
DD (1)	DD202022A5 (fr)
DE (1)	DE3168082D1 (fr)
DK (1)	DK170976B1 (fr)
HU (1)	HU193147B (fr)
IL (1)	IL64120A (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4389528A (en) *	1980-10-31	1983-06-21	Fmc Corporation	Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates
US4428765A (en)	1981-10-05	1984-01-31	Monsanto Company	Thiosulfenamide derivatives of N-phosphonomethylglycine triesters as herbicides
JPS59167566A (ja) *	1983-03-11	1984-09-21	Otsuka Chem Co Ltd	アミノスルフエニルカ−バメイト誘導体の精製方法
GB8316845D0 (en) *	1983-06-21	1983-07-27	Fbc Ltd	Insecticides
US4587353A (en) *	1983-08-23	1986-05-06	Ciba-Geigy Corporation	Process for producing N-chlorosulfenyl compounds
JPS60146927A (ja) *	1983-12-31	1985-08-02	Takeo Takagaki	往復運動を回転運動に変える機構に用いるフリ−ホイ−ル
NL1015313C2 (nl) *	2000-05-26	2001-11-27	Dsm Nv	Werkwijze voor de bereiding van enantiomeer verrijkte esters en alcoholen.
EP2151437A4 (fr)	2007-03-07	2012-05-02	Nissan Chemical Ind Ltd	Composé de benzamide substitué par isoxazoline et agent de contrôle des nuisibles
WO2009005015A1 (fr)	2007-06-29	2009-01-08	Nissan Chemical Industries, Ltd.	Composé isoxazoline ou énone oxime substitué, et agent de lutte contre les nuisibles
WO2009072621A1 (fr)	2007-12-07	2009-06-11	Nissan Chemical Industries, Ltd.	Composé dihydroazole substitué et agent antiparasitaire
UA115666C2 (uk)	2012-07-12	2017-12-11	Ніссан Кемікал Індастріз, Лтд.	Заміщена оксимом амідна сполука і засіб для боротьби зі шкідниками
CN111138330B (zh) *	2019-12-25	2021-12-17	湖南海利常德农药化工有限公司	双二正丁胺二硫的合成方法
CN118324677B (zh) *	2024-04-12	2024-10-01	江苏三吉利化工股份有限公司	一种丁硫残杀威的合成方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3847951A (en) *	1972-02-28	1974-11-12	Chevron Res	Insecticidal n-thio-substituted carbamates of dihydrobenzofuranols
US3897463A (en) *	1972-12-21	1975-07-29	Gustave K Kohn	Insecticidal N-thio-substituted carbamates of dihydrobenzofuranols
US3997549A (en) *	1973-03-12	1976-12-14	The Regents Of The University Of California	N-arylsulfenylated derivatives of benzofuranyl methylcarbamates
US4006231A (en) *	1973-07-12	1977-02-01	The Regents Of The University Of California	N-aminosulfenylated derivatives of carbofuran
DE2344175A1 (de) *	1973-09-01	1975-03-27	Bayer Ag	N-sulfenylierte 2,3-dihydrobenzofuranyl7-n-methylcarbamate, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide
DE2428924A1 (de) *	1974-06-15	1976-01-02	Bayer Ag	N-sulfenylierte arylcarbamate, verfahren zu ihrer herstellung und ihre insektizide verwendung
US4108991A (en) *	1976-12-06	1978-08-22	The Regents Of The University Of California	N-aminosulfenyl derivatives of aldicarb
US4254136A (en) *	1978-08-31	1981-03-03	Ciba-Geigy Corporation	Phenolic esters of N-trialkylureidothio-N-methyl carbamic acids useful as insecticides

1980
- 1980-10-31 US US06/202,526 patent/US4329293A/en not_active Expired - Lifetime
1981
- 1981-10-13 CA CA000387772A patent/CA1173053A/fr not_active Expired
- 1981-10-22 BR BR8106825A patent/BR8106825A/pt unknown
- 1981-10-26 IL IL64120A patent/IL64120A/xx not_active IP Right Cessation
- 1981-10-28 EP EP81109128A patent/EP0051273B1/fr not_active Expired
- 1981-10-28 DE DE8181109128T patent/DE3168082D1/de not_active Expired
- 1981-10-29 JP JP56172202A patent/JPS5941990B2/ja not_active Expired
- 1981-10-30 DK DK479781A patent/DK170976B1/da active
- 1981-10-30 HU HU813198A patent/HU193147B/hu unknown
- 1981-10-30 KR KR1019810004182A patent/KR850000926B1/ko not_active Expired
- 1981-10-30 DD DD81234496A patent/DD202022A5/de unknown
1982
- 1982-12-20 JP JP57222235A patent/JPS6014022B2/ja not_active Expired

Also Published As

Publication number	Publication date
IL64120A (en)	1985-06-30
JPS6014022B2 (ja)	1985-04-11
DE3168082D1 (en)	1985-02-14
CA1173053A (fr)	1984-08-21
IL64120A0 (en)	1982-01-31
JPS57112366A (en)	1982-07-13
DK479781A (da)	1982-05-01
KR850000926B1 (ko)	1985-06-28
US4329293A (en)	1982-05-11
EP0051273A1 (fr)	1982-05-12
JPS5941990B2 (ja)	1984-10-11
JPS58116456A (ja)	1983-07-11
DK170976B1 (da)	1996-04-09
KR830007610A (ko)	1983-11-04
EP0051273B1 (fr)	1985-01-02
HU193147B (en)	1987-08-28
BR8106825A (pt)	1982-07-06

Publication	Publication Date	Title
DE69534190T2 (de)	2005-09-29	Verfahren zur Herstellung von 1,2-Benzisothiazol-3-onen
DE69813312T2 (de)	2004-02-19	Verfahren zur herstellung von cyclopropylethyn sowie zwischenprodukte zur herstellung von cyclopropylethyn
DD202022A5 (de)	1983-08-24	Verfahren zur sulfenylierung von n-alkylcarbamaten
DE2500265A1 (de)	1976-07-08	Neue mikrobizide
DE2130919C3 (de)	1978-06-01	Substituierte Diphenylether, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE69632919T2 (de)	2005-07-28	Verfahren zur herstellung von 2-chlor-5-chloromethyl-thiazol
CH632501A5 (de)	1982-10-15	Verfahren zur herstellung von 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-onen.
DE69013726T2 (de)	1995-05-11	Verbessertes Verfahren für die Herstellung von o-Carboxypyridyl- und o-Carboxychinolylimidazolinonen.
DE60222376T2 (de)	2008-05-29	Verfahren zur Herstellung von Diazonaphthochinonsulfonylchloriden mit Diphosgen und Triphosgen
EP1127879A1 (fr)	2001-08-29	Procédé pour la préparation de l'acide 1,3-dibenzyle-imidazolidine-2-one- cis-4,5 dicarboxylique et son anhydride
EP0092111B1 (fr)	1985-11-21	Dérivés du 2,2-dihalogène-3,3-diméthylcyclopropane
DE2330241C3 (de)	1980-10-09	Chlorthio-N-phthalimid, Verfahren zu seiner Herstellung und seine Verwendung
DE2438077A1 (de)	1975-03-20	Verfahren zur herstellung von propanolaminderivaten und nach dem verfahren hergestellte propanolaminderivate
DE2936288A1 (de)	1980-03-20	Verfahren zur herstellung von 2,2'-bis- eckige klammer auf 4-(1,1,3,3-tetramethylbutyl)-phenol eckige klammer zu -sulfid
EP0834506B1 (fr)	2004-01-14	Procédé pour la préparation des (9alpha, 13alpha, 14alpha)-1-(3-Méthoxymorphinan-17-yl)alkanones
DE3111518A1 (de)	1982-02-18	Salze von carbamoylsulfonsaeurederivaten und verfahren zu ihrer herstellung
DE3040633A1 (de)	1981-05-21	Verfahren zur herstellung von carbaminsaeurephenylesterderivaten durch acylierung sowie dafuer verwendete acylierungsmittel
DE2814453A1 (de)	1978-10-19	Carbamoyloxyphenyl-verbindungen
DE1618913C (de)	1973-08-09	Verfahren zur Herstellung von Alkylthioaldoximen
WO2001085679A1 (fr)	2001-11-15	Procede pour la production de sels de sulfonyl-benzoyl guanidinium
EP4377294A1 (fr)	2024-06-05	Procédé de préparation de dérivés de (2,2,2-trifluoroéthyl)sulfanylaniline
DE804572C (de)	1951-04-26	Verfahren zur Herstellung von Sulfensaeurehalogeniden
DE952084C (de)	1956-11-08	Verfahren zur Herstellung von organischen Isothiocyanaten
DE3425138A1 (de)	1986-01-16	Verfahren zur herstellung eines optisch aktiven phenoxypropionsaeure-ester-derivates
DE1543942C (de)	1971-08-05	Verfahren zur Herstellung von 1 Oxa 2 methyl 3 carbonylarmno 4 tnia cyclohe xen(2)en