CA1118436A - Procede d'obtention de composes du type organothioaldoxime - Google Patents

Procede d'obtention de composes du type organothioaldoxime

Info

Publication number: CA1118436A
Authority: CA; Canada
Prior art keywords: process according; reaction; weight; aldoxime; polyhydric alcohol
Prior art date: 1979-01-15
Legal status (The legal status 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 status listed.): Expired

Application number

CA000319666A

Other languages

English (en)

Inventor

John K. Chan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide 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.)

1979-01-15

Filing date

1979-01-15

Publication date

1982-02-16

1979-01-15 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1979-01-15 Priority to CA000319666A priority Critical patent/CA1118436A/fr

1982-02-16 Application granted granted Critical

1982-02-16 Publication of CA1118436A publication Critical patent/CA1118436A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 title claims description 14
238000000034 method Methods 0.000 claims abstract description 44
230000008569 process Effects 0.000 claims abstract description 36
150000005846 sugar alcohols Polymers 0.000 claims abstract description 12
125000004122 cyclic group Chemical group 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 30
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 7
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
239000000600 sorbitol Substances 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 2
239000004386 Erythritol Substances 0.000 claims description 2
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
235000019414 erythritol Nutrition 0.000 claims description 2
229940009714 erythritol Drugs 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004966 cyanoalkyl group Chemical group 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000004971 nitroalkyl group Chemical group 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 17
239000003125 aqueous solvent Substances 0.000 abstract description 2
159000000000 sodium salts Chemical class 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
239000000376 reactant Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
-1 aralkyl compound Chemical class 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
OQGRONGNRFBIMU-UHFFFAOYSA-N methyl 2-hydroxyethanimidothioate Chemical compound CSC(=N)CO OQGRONGNRFBIMU-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000003518 caustics Substances 0.000 description 6
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 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
239000006227 byproduct Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000011591 potassium Substances 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
SYJPAKDNFZLSMV-HWKANZROSA-N (E)-2-methylpropanal oxime Chemical compound CC(C)\C=N\O SYJPAKDNFZLSMV-HWKANZROSA-N 0.000 description 1
IFDZZSXEPSSHNC-ONEGZZNKSA-N (ne)-n-propylidenehydroxylamine Chemical compound CC\C=N\O IFDZZSXEPSSHNC-ONEGZZNKSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Chemical compound OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007805 chemical reaction reactant Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 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
VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000010355 oscillation Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000319666A 1979-01-15 1979-01-15 Procede d'obtention de composes du type organothioaldoxime Expired CA1118436A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000319666A CA1118436A (fr)	1979-01-15	1979-01-15	Procede d'obtention de composes du type organothioaldoxime

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000319666A CA1118436A (fr)	1979-01-15	1979-01-15	Procede d'obtention de composes du type organothioaldoxime

Publications (1)

Publication Number	Publication Date
CA1118436A true CA1118436A (fr)	1982-02-16

Family

ID=4113335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000319666A Expired CA1118436A (fr)	1979-01-15	1979-01-15	Procede d'obtention de composes du type organothioaldoxime

Country Status (1)

Country	Link
CA (1)	CA1118436A (fr)

1979
- 1979-01-15 CA CA000319666A patent/CA1118436A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-02-16	MKEX	Expiry

Publication	Publication Date	Title
KR920010393B1 (ko)	1992-11-27	헤테로아릴옥시아세트아미드의 제조방법
EP0547825A2 (fr)	1993-06-23	Procédé de préparation d'alpha-céto-amides
US6657085B2 (en)	2003-12-02	Process for the preparation of aniline compounds
KR840001923B1 (ko)	1984-10-25	2-메르캅토에틸아민 할로겐화수소산염류의 제조방법
CA1118436A (fr)	1982-02-16	Procede d'obtention de composes du type organothioaldoxime
US4144261A (en)	1979-03-13	Process for preparing organothio-aldoxime compounds
EP0258999B1 (fr)	1991-05-02	Procédé pour la préparation d'isothiazolones
US5650542A (en)	1997-07-22	Process for the preparation of 2-chloro-6-nitrophenyl alkyl sulphides and novel 2-chloro-6-nitrophenyl alkyl sulphides
GB2039474A (en)	1980-08-13	Process for preparing organothio-aldoximes
US4359428A (en)	1982-11-16	Preparation of fluorinated anthranilic acid and anthranilonitrile
US4391759A (en)	1983-07-05	Process for the preparation of organothioaldoxime compounds
US4058549A (en)	1977-11-15	N-substituted cyanoalkane-sulfenyl (and thiosulfenyl)-N-alkyl carbamoyl halides
EP0341585B1 (fr)	1993-01-13	Préparation du 3,5,6-trichloro-pyridine-2-ol et produits intermédiaires a cet effet
KR20010007081A (ko)	2001-01-26	Ｎ,ｎ-디알킬아릴아민 촉매의 존재하에서ｎ-알크(엔)옥시(또는 아릴옥시)카보닐이소티오시아네이트 및 그의 유도체를 제조하는 방법
KR950008208B1 (ko)	1995-07-26	메르캅토벤조에이트의 제조방법
US6066754A (en)	2000-05-23	Process for manufacturing N-alkoxy(or aryloxy)carbonyl isothiocyanate derivatives using N,N-dialkylarylamine as catalyst
JP4041881B2 (ja)	2008-02-06	新規なｎ−チオ置換複素環化合物およびその製造方法
RU2193034C2 (ru)	2002-11-20	Способ получения производных 2-аминотиазолкарбоксамида
KR0156869B1 (ko)	1998-12-01	신규 디술피드 화합물
US4001353A (en)	1977-01-04	Preparation of o,s-dimethyl-thiol-phosphoric acid diester-amide
EP1919860A1 (fr)	2008-05-14	Procede a haut rendement pour l'elaboration de thioalkylamines
KR910004177B1 (ko)	1991-06-24	아닐리노 피리미딘 유도체
US4898942A (en)	1990-02-06	Process for manufacturing diazinon
US4536353A (en)	1985-08-20	Process for preparing α-ketonitriles
EP0162404B1 (fr)	1988-08-24	Procédé de préparation de 2-alcoyl-5-haloacétylbenzène-sulfonamides