CH624946A5 - Process for the preparation of N-substituted oxazolidines - Google Patents

Process for the preparation of N-substituted oxazolidines Download PDF

Info

Publication number: CH624946A5
Authority: CH; Switzerland
Prior art keywords: hydrogen; lower alkyl; formula; alkyl; phenyl
Prior art date: 1975-08-28

Application number

CH1064076A

Other languages

German (de)

English (en)

Inventor

Harold M Pitt

Original Assignee

Stauffer Chemical Co

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.)

1975-08-28

Filing date

1976-08-20

Publication date

1981-08-31

1976-08-20 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1981-08-31 Publication of CH624946A5 publication Critical patent/CH624946A5/de

Links

-1 N-substituted oxazolidines Chemical class 0.000 title claims description 31
238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229910000039 hydrogen halide Inorganic materials 0.000 claims description 12
239000012433 hydrogen halide Substances 0.000 claims description 12
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
238000009833 condensation Methods 0.000 claims description 9
230000005494 condensation Effects 0.000 claims description 9
125000001188 haloalkyl group Chemical group 0.000 claims description 9
150000001728 carbonyl compounds Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
229910014033 C-OH Inorganic materials 0.000 claims 1
229910014570 C—OH Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
239000000047 product Substances 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
150000002917 oxazolidines Chemical class 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000000370 acceptor Substances 0.000 description 14
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 11
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000000243 solution Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
238000004140 cleaning Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000002262 Schiff base Substances 0.000 description 4
150000004753 Schiff bases Chemical class 0.000 description 4
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 description 3
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
VSHIRTNKIXRXMI-UHFFFAOYSA-N 2,2-dimethyl-1,3-oxazolidine Chemical compound CC1(C)NCCO1 VSHIRTNKIXRXMI-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
229940102253 isopropanolamine Drugs 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
XMPCGZCCOXWBKR-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-oxazolidine Chemical compound CC1CNC(C)(C)O1 XMPCGZCCOXWBKR-UHFFFAOYSA-N 0.000 description 1
101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
101100491995 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-1 gene Proteins 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
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 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical group C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1064076A 1975-08-28 1976-08-20 Process for the preparation of N-substituted oxazolidines CH624946A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60847575A	1975-08-28	1975-08-28

Publications (1)

Publication Number	Publication Date
CH624946A5 true CH624946A5 (en)	1981-08-31

Family

ID=24436651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1064076A CH624946A5 (en)	1975-08-28	1976-08-20	Process for the preparation of N-substituted oxazolidines

Country Status (18)

Country	Link
JP (1)	JPS5925788B2 (fr)
BE (1)	BE845577A (fr)
BG (1)	BG27551A3 (fr)
BR (1)	BR7605610A (fr)
CA (1)	CA1075701A (fr)
CH (1)	CH624946A5 (fr)
CS (1)	CS191316B2 (fr)
DD (1)	DD127680A5 (fr)
DE (1)	DE2637580C2 (fr)
FR (1)	FR2322141B1 (fr)
HU (1)	HU174379B (fr)
IL (1)	IL50192A (fr)
IT (1)	IT1066346B (fr)
NL (1)	NL181274C (fr)
PL (1)	PL100986B1 (fr)
RO (1)	RO69421A (fr)
SU (2)	SU814276A3 (fr)
YU (2)	YU40284B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5225570A (en) *	1987-08-13	1993-07-06	Monsanto Company	5-heterocyclic-substituted oxazolidine dihaloacetamides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1419330A1 (de) *	1962-06-09	1970-02-19	Hoechst Ag	Optische Aufhellungsmittel
BE757717A (fr) *	1969-10-21	1971-04-01

1976
- 1976-07-30 CA CA258,154A patent/CA1075701A/fr not_active Expired
- 1976-08-03 IL IL50192A patent/IL50192A/xx unknown
- 1976-08-20 CH CH1064076A patent/CH624946A5/de not_active IP Right Cessation
- 1976-08-20 RO RO7687340A patent/RO69421A/fr unknown
- 1976-08-20 DE DE2637580A patent/DE2637580C2/de not_active Expired - Lifetime
- 1976-08-21 JP JP51100109A patent/JPS5925788B2/ja not_active Expired
- 1976-08-23 BR BR7605610A patent/BR7605610A/pt unknown
- 1976-08-25 PL PL1976191993A patent/PL100986B1/pl unknown
- 1976-08-25 YU YU2076/76A patent/YU40284B/xx unknown
- 1976-08-26 BG BG034079A patent/BG27551A3/xx unknown
- 1976-08-26 IT IT51031/76A patent/IT1066346B/it active
- 1976-08-26 BE BE7000872A patent/BE845577A/xx not_active IP Right Cessation
- 1976-08-26 DD DD194486A patent/DD127680A5/xx unknown
- 1976-08-27 NL NLAANVRAGE7609563,A patent/NL181274C/xx not_active IP Right Cessation
- 1976-08-27 HU HU76SA2966A patent/HU174379B/hu unknown
- 1976-08-27 SU SU762391502A patent/SU814276A3/ru active
- 1976-08-27 CS CS765587A patent/CS191316B2/cs unknown
- 1976-08-27 FR FR7625928A patent/FR2322141B1/fr not_active Expired
1978
- 1978-04-27 SU SU782607602A patent/SU727145A3/ru active
1982
- 1982-10-14 YU YU02318/82A patent/YU231882A/xx unknown

Also Published As

Publication number	Publication date
FR2322141B1 (fr)	1980-04-04
HU174379B (hu)	1979-12-28
SU727145A3 (ru)	1980-04-05
BR7605610A (pt)	1977-08-09
CS191316B2 (en)	1979-06-29
NL7609563A (nl)	1977-03-02
IT1066346B (it)	1985-03-04
JPS5925788B2 (ja)	1984-06-21
YU231882A (en)	1983-02-28
RO69421A (fr)	1981-06-30
PL100986B1 (pl)	1978-11-30
DE2637580C2 (de)	1990-08-02
IL50192A0 (en)	1976-10-31
SU814276A3 (ru)	1981-03-15
FR2322141A1 (fr)	1977-03-25
NL181274C (nl)	1987-07-16
YU207676A (en)	1983-02-28
YU40284B (en)	1985-12-31
IL50192A (en)	1978-10-31
BE845577A (nl)	1977-02-28
BG27551A3 (en)	1979-11-12
DE2637580A1 (de)	1977-03-17
JPS5236662A (en)	1977-03-22
DD127680A5 (de)	1977-10-05
CA1075701A (fr)	1980-04-15

Legal Events

Date	Code	Title	Description
1996-09-13	PL	Patent ceased

Publication	Publication Date	Title
DE1493856A1 (de)	1969-10-09	Verfahren zur Herstellung von optisch aktiven Verbindungen
DE1088965B (de)	1960-09-15	Verfahren zur Herstellung von neuen Umsetzungsprodukten des 2, 3-Dimercaptochinoxalins
DE2434549A1 (de)	1976-01-29	Verfahren zur herstellung des suesstoffes 6-methyl-3,4-dihydro-1,2,3-oxathiazin4-on-2,2-dioxid
DE915809C (de)	1954-07-29	Verfahren zur Herstellung von heterocyclischen Sulfonamiden
CH640835A5 (de)	1984-01-31	Verfahren zur herstellung von 3-hydroxy-5-halogenpyridinen.
DE946804C (de)	1956-08-09	Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure
DE1300117B (de)	1969-07-31	5-Sulfonyl-1, 2-dithiol-3-one
DE2637580C2 (de)	1990-08-02	Verfahren zur herstellung von n-substituierten oxazolidinen
DE3017977A1 (de)	1981-11-19	Neue substituierte 2(3h)-benzothiazolone
DE1078582B (de)	1960-03-31	Verfahren zur Herstellung substituierter Thyropropionsaeuren
EP0224849B1 (fr)	1989-02-15	4-Mercaptobenzonitriles et leur procédé de préparation
DE1121052B (de)	1962-01-04	Verfahren zur Herstellung von 4, 5-substituierten 2-Amino-oxazolen
DE1793594C3 (de)	1976-03-18	Verfahren zur Herstellung von substituierten Acrylnitrilen
DE3241114A1 (de)	1984-05-10	Verfahren zur herstellung von 1-amino-1,3,5-triazin-2,4-(1h,3h)dionen
DE954332C (de)	1956-12-13	Verfahren zur Herstellung neuer Ester
DE1298092B (de)	1969-06-26	Arylthiocarbamate
DE957123C (de)	1957-01-31	Verfahren zur Herstellung von Thioabkoemmlingen der Colchiceine
AT278837B (de)	1970-02-10	Verfahren zur Herstellung von neuen 4-[5-Nitrothiazolyl-(2)]-thiomorpholin-1-oxyden und 1,1-dioxyden
DE2008272C3 (de)	1978-01-19	Verfahren zur Racemisierung und Auftrennung eines Salzes einer 2-(2-NaphthyO-propionsäure und einer stickstoffhaltigen Base
AT220149B (de)	1962-03-12	Verfahren zur Herstellung von Aryloxymethyl-2-oxazolidinonen
DE1147584B (de)	1963-04-25	Verfahren zur Herstellung von substituierten 2-Mercaptothiazol-5-aldehyden
DE913215C (de)	1954-09-06	Verfahren zur Herstellung von gegebenenfalls am mittelstaendigen Kohlenstoffatom der Methinkette substituierten symmetrischen und unsymmetrischen Trimethincarbocyanin-Farbstoffen
AT364836B (de)	1981-11-25	Verfahren zur herstellung von neuen o-substituierten derivaten des (+)-cyanidan-3-ols und deren salzen
DE913214C (de)	1954-06-26	Verfahren zur Herstellung von Merocyaninen, die in der Kette substituiert sind
AT214454B (de)	1961-04-10	Verfahren zur Herstellung neuer Phosphinsäurederivate