CH616405A5 - - Google Patents

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Info

Publication number: CH616405A5
Authority: CH; Switzerland
Prior art keywords: butynyl; carbamate; dimethylformamide; thionyl chloride; chlorophenyl
Prior art date: 1975-11-24

Application number

CH1479876A

Other languages

English (en)

French (fr)

Inventor

Jerry L Rutter

Original Assignee

Gulf Oil 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.)

1975-11-24

Filing date

1976-11-24

Publication date

1980-03-31

1976-11-24 Application filed by Gulf Oil Corp filed Critical Gulf Oil Corp

1980-03-31 Publication of CH616405A5 publication Critical patent/CH616405A5/fr

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 57
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 37
MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 22
238000000034 method Methods 0.000 claims description 15
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 12
ACYQQFWLJXHFND-UHFFFAOYSA-N 4-hydroxybut-2-ynyl n-(3-chlorophenyl)carbamate Chemical compound OCC#CCOC(=O)NC1=CC=CC(Cl)=C1 ACYQQFWLJXHFND-UHFFFAOYSA-N 0.000 claims description 10
239000012320 chlorinating reagent Substances 0.000 claims description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
238000005660 chlorination reaction Methods 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
VSKFADHADUWCCL-UHFFFAOYSA-N carbamoperoxoic acid Chemical compound NC(=O)OO VSKFADHADUWCCL-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
125000003568 4-hydroxy-2-butynyl group Chemical group [H]OC([H])([H])C#CC([H])([H])* 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000001737 promoting effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
-1 4-chloro-2-butynyl Chemical group 0.000 description 1
RPUJAOFSZSEVPC-UHFFFAOYSA-N 4-chlorobut-2-yn-1-ol Chemical compound OCC#CCCl RPUJAOFSZSEVPC-UHFFFAOYSA-N 0.000 description 1
KKTHKTQIFWSVFZ-UHFFFAOYSA-N 4-hydroxybut-2-ynyl carbamate Chemical compound NC(=O)OCC#CCO KKTHKTQIFWSVFZ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001361 allenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HDHXNQZPJLXWJK-UHFFFAOYSA-N carbonyl dichloride;n,n-dimethylformamide Chemical compound ClC(Cl)=O.CN(C)C=O HDHXNQZPJLXWJK-UHFFFAOYSA-N 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000017105 transposition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CH1479876A 1975-11-24 1976-11-24 CH616405A5 (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/634,575 US4012433A (en)	1975-11-24	1975-11-24	Process for manufacturing 4-chloro-2-butynyl m-chlorocarbanilate

Publications (1)

Publication Number	Publication Date
CH616405A5 true CH616405A5 (pt)	1980-03-31

Family

ID=24544360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1479876A CH616405A5 (pt)	1975-11-24	1976-11-24

Country Status (21)

Country	Link
US (1)	US4012433A (pt)
JP (1)	JPS5817458B2 (pt)
AT (1)	AT346358B (pt)
AU (1)	AU499597B2 (pt)
BE (1)	BE848698A (pt)
CA (1)	CA1074809A (pt)
CH (1)	CH616405A5 (pt)
DE (1)	DE2653150C2 (pt)
DK (1)	DK526676A (pt)
FI (1)	FI63219C (pt)
FR (1)	FR2332262A1 (pt)
GB (1)	GB1499311A (pt)
GR (1)	GR61819B (pt)
IE (1)	IE44314B1 (pt)
IN (1)	IN143578B (pt)
MX (1)	MX4020E (pt)
NL (1)	NL7613112A (pt)
PT (1)	PT65878B (pt)
SE (1)	SE433611B (pt)
TR (1)	TR19454A (pt)
ZA (1)	ZA766998B (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02118051U (pt) *	1989-03-07	1990-09-21
US7346643B1 (en) *	1999-07-30	2008-03-18	Mips Technologies, Inc.	Processor with improved accuracy for multiply-add operations
WO2016202894A1 (en)	2015-06-17	2016-12-22	Universitaet Des Saarlandes	Method of converting alcohol to halide
CN110655446A (zh) *	2019-10-22	2020-01-07	邹平铭兴化工有限公司	氯代异丁烷的化学合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE113716C (pt) *
ZA591098B (pt) *	1958-03-24
DE1133716B (de) *	1960-11-26	1962-07-26	Basf Ag	Verfahren zur Herstellung von aliphatischen Di- und Polychlor-verbindungen
DE1135893B (de) *	1961-05-19	1962-09-06	Basf Ag	Verfahren zur Herstellung von Chlorkohlenwasserstoffen der Acetylenreihe

1975
- 1975-11-24 US US05/634,575 patent/US4012433A/en not_active Expired - Lifetime
1976
- 1976-11-23 DE DE2653150A patent/DE2653150C2/de not_active Expired
- 1976-11-23 CA CA266,358A patent/CA1074809A/en not_active Expired
- 1976-11-23 DK DK526676A patent/DK526676A/da not_active Application Discontinuation
- 1976-11-23 ZA ZA766998A patent/ZA766998B/xx unknown
- 1976-11-24 IE IE2585/76A patent/IE44314B1/en unknown
- 1976-11-24 CH CH1479876A patent/CH616405A5/fr not_active IP Right Cessation
- 1976-11-24 MX MX765151U patent/MX4020E/es unknown
- 1976-11-24 SE SE7613122A patent/SE433611B/xx unknown
- 1976-11-24 FI FI763383A patent/FI63219C/fi not_active IP Right Cessation
- 1976-11-24 AT AT871876A patent/AT346358B/de not_active IP Right Cessation
- 1976-11-24 IN IN2106/CAL/76A patent/IN143578B/en unknown
- 1976-11-24 FR FR7635337A patent/FR2332262A1/fr active Granted
- 1976-11-24 NL NL7613112A patent/NL7613112A/xx not_active Application Discontinuation
- 1976-11-24 BE BE172655A patent/BE848698A/xx not_active IP Right Cessation
- 1976-11-24 AU AU19982/76A patent/AU499597B2/en not_active Expired
- 1976-11-24 PT PT65878A patent/PT65878B/pt unknown
- 1976-11-24 JP JP51140273A patent/JPS5817458B2/ja not_active Expired
- 1976-11-24 GR GR52253A patent/GR61819B/el unknown
- 1976-11-24 GB GB49044/76A patent/GB1499311A/en not_active Expired
- 1976-11-24 TR TR19454A patent/TR19454A/xx unknown

Also Published As

Publication number	Publication date
DE2653150A1 (de)	1977-06-02
IE44314L (en)	1977-05-24
FI63219C (fi)	1983-05-10
NL7613112A (nl)	1977-05-26
MX4020E (es)	1981-11-03
US4012433A (en)	1977-03-15
SE7613122L (sv)	1977-05-25
AU1998276A (en)	1978-06-01
IE44314B1 (en)	1981-10-21
AU499597B2 (en)	1979-04-26
TR19454A (tr)	1979-02-27
CA1074809A (en)	1980-04-01
GB1499311A (en)	1978-02-01
IN143578B (pt)	1977-12-31
FI63219B (fi)	1983-01-31
PT65878A (en)	1976-12-01
JPS5817458B2 (ja)	1983-04-07
SE433611B (sv)	1984-06-04
ATA871876A (de)	1978-03-15
PT65878B (en)	1978-05-18
FR2332262B1 (pt)	1980-11-21
FR2332262A1 (fr)	1977-06-17
GR61819B (en)	1979-01-22
FI763383A (pt)	1977-05-25
DK526676A (da)	1977-05-25
JPS5278850A (en)	1977-07-02
BE848698A (fr)	1977-05-24
DE2653150C2 (de)	1985-02-07
ZA766998B (en)	1977-10-26
AT346358B (de)	1978-11-10

Legal Events

Date	Code	Title	Description
1980-11-14	PUE	Assignment	Owner name: VELSICOL CHEMICAL CORPORATION
1986-07-31	PL	Patent ceased

Publication	Publication Date	Title
EP0907635B1 (en)	2002-09-25	Halogen substituted carbamate compounds from 2-phenyl-1,2-ethanediol
FR2696458A1 (fr)	1994-04-08	Procédé de préparation de dérivés du taxane.
CH636848A5 (fr)	1983-06-30	Procede de production de n,n-di(ethyl)-meta-toluamide.
FR2599739A1 (fr)	1987-12-11	Acides biphenyl hydroxamiques a action therapeutique
FR2479209A1 (fr)	1981-10-02	Procede de preparation d'esters d'acide carbamique n-monosubstitues
CA1077061A (fr)	1980-05-06	Procede d'oxydation de cetones .beta.-ethyleniques
CH616405A5 (pt)	1980-03-31
CA2374553A1 (fr)	2000-12-21	Sulfonylamides et carboxamides et leur application en catalyse asymetrique
EP0078729B1 (fr)	1986-01-08	Procédé de fabrication d'isocyanates aromatiques par carbonylation des dérivés nitrés en présence de catalyseurs supportés préparés à partir de complexes hétéropolymétalliques
EP0842148B1 (fr)	2000-12-20	Derives de benzenesulfonamide, leur preparation et leurs applications en therapeutique
FR2481699A1 (fr)	1981-11-06	Preparation de carbamates n-monosubstitues
FR2464248A1 (fr)	1981-03-06	Procede de preparation de b-aminopropionamides
EP0019517B1 (fr)	1982-05-19	Procédé de préparation des isocyanates organiques à partir des dérivés nitrés
EP0723955A1 (fr)	1996-07-31	Procédé de synthèse de carbodiimides substitués
CH619928A5 (pt)	1980-10-31
EP0585165B1 (fr)	1997-06-04	Procédé de préparation d'isocyanates d'acyle
US5654461A (en)	1997-08-05	Sulfamate compound containing carbamoyl group
FR2769911A1 (fr)	1999-04-23	Procede pour preparer des derives de 5-perfluoroalkyluracile
DE69509745T2 (de)	1999-12-09	Neue carbamatverbindungen und verfahren zu ihrer herstellung
EP0529444B1 (de)	1997-04-16	2-Arylpropensäuren und ihre Verwendung bei der Herstellung von S-Ketoprofen
EP0828740B1 (fr)	2001-09-05	Derives du 2-azabicyclo[2.2.1]heptane, leur preparation et leur application
SU633856A1 (ru)	1978-11-25	Способ получени 3-(ариламино)бутинов-1
CH621542A5 (en)	1981-02-13	Process for the preparation of isothioureidobenzenes
CH653016A5 (fr)	1985-12-13	Derives du chlorure d'aminosulfenyle, procede pour la preparation de ceux-ci et utilisation de ces derives pour la preparation de carbamates.
FR2649103A1 (pt)	1991-01-04