GB597446A - Improvements in or relating to organic compounds containing sulphur - Google Patents
Improvements in or relating to organic compounds containing sulphurInfo
- Publication number
- GB597446A GB597446A GB2103845A GB2103845A GB597446A GB 597446 A GB597446 A GB 597446A GB 2103845 A GB2103845 A GB 2103845A GB 2103845 A GB2103845 A GB 2103845A GB 597446 A GB597446 A GB 597446A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- product
- carbon disulphide
- iodide
- methyl iodide
- 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
- 150000002894 organic compounds Chemical class 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000005864 Sulphur Substances 0.000 title 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 9
- 229940100198 alkylating agent Drugs 0.000 abstract 5
- 239000002168 alkylating agent Substances 0.000 abstract 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 159000000000 sodium salts Chemical class 0.000 abstract 4
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 2
- -1 alkyl p-toluene sulphonate Chemical compound 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 2
- 238000000197 pyrolysis Methods 0.000 abstract 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organic compounds containing the structure <FORM:0597446/IV/1> or tautomers thereof are prepared by reacting, preferably in a medium substantially free from any hydroxylic solvent (e.g. in diethyl ether), carbon disulphide with a dry alkali-metal derivative of a compound of the general formula Q-CH2-COOR1 wherein Q represents -COOR2, -COR3 (which is generally hydrolysed away during the reaction), or -CN, and R1, R2 and R3 are each a hydrocarbon group, preferably an alkyl group, and reacting the product with an alkyl salt or ester. The alkyl group in the alkylating agent may contain substituents, which in some cases, such as that of chloracetic ethyl ester, may lead to a further condensation to form compounds in which the <FORM:0597446/IV/2> grouping forms part of a ring. Such compounds are also obtained by effecting the alkylation with di-salts or di-esters, e.g. alkylene dihalides such as ethylene dibromide or trimethylene dibromide or trimethylene dibromide. Specified monovalent alkylating agents are methyl, ethyl and higher alkyl halides, of which the iodides are particularly suitable, dialkyl sulphates, e.g. dimethyl or diethyl sulphate, alkyl p-toluene sulphonate and benzyl halides or sulphates. The products may be further subjected to alkaline hydrolysis, which may be followed by dry distillation. In examples: (1) the sodium salt of diethyl malonate is reacted with carbon disulphide in anhydrous ethyl ether and the product alkylated with methyl iodide; (2) as in (1) with ethyl alcohol present; the product on hydrolysis with alcoholic caustic potash and dry distillation yields ketene dimercaptal; (3) the sodium salt of ethyl acetoacetate in anhydrous ethyl ether is reacted with carbon disulphide, refluxed with ethyl alcohol and alkylated with methyl iodide; (4) the sodium salt of ethyl cyanacetate is reacted with carbon disulphide in anhydrous ether and the product alkylated with methyl iodide; (5) as in (2), but instead of alkylating with methyl iodide the product is refluxed with ethyl chloracetate; (6) the sodium salt of diethyl malonate with carbon disulphide in anhydrous ether is reacted and the product alkylated with ethylene dibromide followed by hydrolysis with sodium hydroxide; (7) as in (4) using ethyl iodide instead of methyl iodide as the alkylating agent; (8) as in (7) using benzyl chloride instead of ethyl iodide as the alkylating agent; (9) as in (7) using trimethylene dibromide instead of ethyl iodide as alkylating agent, followed by hydrolysis and distillation in vacuo. Specification 549,201 is referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB597446A true GB597446A (en) | 1948-01-27 |
Family
ID=1735877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2103845A Expired GB597446A (en) | 1945-08-17 | Improvements in or relating to organic compounds containing sulphur |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB597446A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542140A (en) * | 1983-10-20 | 1985-09-17 | American Home Products Corporation | Pyridinyl substituted ketenemercaptal derivatives |
-
1945
- 1945-08-17 GB GB2103845A patent/GB597446A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542140A (en) * | 1983-10-20 | 1985-09-17 | American Home Products Corporation | Pyridinyl substituted ketenemercaptal derivatives |
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