GB1282493A - A process for the preparation of dithioesters - Google Patents
A process for the preparation of dithioestersInfo
- Publication number
- GB1282493A GB1282493A GB5281569A GB5281569A GB1282493A GB 1282493 A GB1282493 A GB 1282493A GB 5281569 A GB5281569 A GB 5281569A GB 5281569 A GB5281569 A GB 5281569A GB 1282493 A GB1282493 A GB 1282493A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- prepared
- dithioesters
- cooh
- reaction
- Prior art date
- 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
Links
- 239000012988 Dithioester Substances 0.000 title abstract 4
- 125000005022 dithioester group Chemical group 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- -1 nitro, phenylazo Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000815 N-oxide group Chemical group 0.000 abstract 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- GUPWNYUKYICHQX-UHFFFAOYSA-N carbonobromidic acid Chemical compound OC(Br)=O GUPWNYUKYICHQX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003982 chlorocarboxylic acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1282493 Dithioesters UNILEVER Ltd 28 Oct 1969 52815/69 Heading C2C Dithioesters of the general formula are prepared by reacting a carboxyalkyl carbodithioate of the formula R. CS. SR<SP>2</SP> wherein R<SP>2</SP> is CH 2 COOH, (CH 2 ) 2 COOH, or CH(Me)CH 2 COOH and R is an organic radical, with a mercaptan of the formula R<SP>1</SP>SH wherein R<SP>1</SP> is an organic radical other than R<SP>2</SP>. The Specification refers to several novel dithioesters, which may be prepared by the above method, in which R is a phenyl group which may be substituted at the 2, 3 or 4 position with any one of an alkoxy, amido, halo, nitro, phenylazo or carbodithioate group, a homocyclic polynuclear aromatic group such as a naphthyl group, a heterocyclic group such as a furyl, 2-pyridyl, substituted 2-pyridyl group or the N-oxide group, or an alkyl group having from 1 to 24 carbon atoms, and in which R<SP>1</SP> is a phenyl group, benzyl group, alkyl or alkenyl group having from 1 to 6 carbon atoms or an alkylcarboxyalkyl group. The reaction is preferably carried out either in an organic solvent e.g. ether or benzene, and the thioglycollic acid by-product is removed by treatment of the reaction mixture with an aqueous alkaline solution e.g. NaOH, or in aqueous solution. The carboxyalkyl carbodithioates may be prepared either by reaction of a Grignard compound with carbon disulphide and subsequent esterification of the magnesium halide salt of the dithioacid with a chlorocarboxylic acid salt, or by thiohydrolysis of S-carboxyalkylthiopiperidinium bromide prepared by reacting a thiopiperide (prepared by the Willgerodt-Kindler method) and a bromocarboxylic acid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5281569A GB1282493A (en) | 1969-10-28 | 1969-10-28 | A process for the preparation of dithioesters |
| CA096,642A CA944350A (en) | 1969-10-28 | 1970-10-27 | Process for the preparation of dithioesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5281569A GB1282493A (en) | 1969-10-28 | 1969-10-28 | A process for the preparation of dithioesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1282493A true GB1282493A (en) | 1972-07-19 |
Family
ID=10465419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5281569A Expired GB1282493A (en) | 1969-10-28 | 1969-10-28 | A process for the preparation of dithioesters |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA944350A (en) |
| GB (1) | GB1282493A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0128833A1 (en) * | 1983-06-10 | 1984-12-19 | Societe Nationale Elf Aquitaine (Production) | Mono and dithio esters, their preparation and uses |
| US7662986B2 (en) * | 1996-07-10 | 2010-02-16 | Commonwealth Scientific And Industrial Research Organisation | Polymerization with living characteristics |
-
1969
- 1969-10-28 GB GB5281569A patent/GB1282493A/en not_active Expired
-
1970
- 1970-10-27 CA CA096,642A patent/CA944350A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0128833A1 (en) * | 1983-06-10 | 1984-12-19 | Societe Nationale Elf Aquitaine (Production) | Mono and dithio esters, their preparation and uses |
| US4594150A (en) * | 1983-06-10 | 1986-06-10 | Societe Nationale Elf Aquitaine (Production) | Mono- and dithioic esters, their preparation and uses |
| US7662986B2 (en) * | 1996-07-10 | 2010-02-16 | Commonwealth Scientific And Industrial Research Organisation | Polymerization with living characteristics |
Also Published As
| Publication number | Publication date |
|---|---|
| CA944350A (en) | 1974-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |