GB863370A - New thiol-sulphoxides, their preparation and use as intermediates - Google Patents
New thiol-sulphoxides, their preparation and use as intermediatesInfo
- Publication number
- GB863370A GB863370A GB2287357A GB2287357A GB863370A GB 863370 A GB863370 A GB 863370A GB 2287357 A GB2287357 A GB 2287357A GB 2287357 A GB2287357 A GB 2287357A GB 863370 A GB863370 A GB 863370A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- thiol
- sulphoxide
- sulphide
- sulphoxides
- 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
- 239000000543 intermediate Substances 0.000 title 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- HRKZEUPYFXLVQW-UHFFFAOYSA-N hydroxysulfanylethane Chemical compound CCSO HRKZEUPYFXLVQW-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- -1 thiol sulphoxide Chemical class 0.000 abstract 2
- 150000003573 thiols Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 abstract 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004969 haloethyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises beta-thiol sulphoxides of the general formula R.SO.CH2CH2SH, wherein R represents an alkyl or aryl group which may be substituted, e.g. by halogen or -CN, the hereinafter described methods of preparing the sulphoxides and a method for converting them into insecticidal thiolo phosphates of the general formula: R.SO.CH2CH2S.P(O)(OR1)(OR2) wherein R is as defined above and R1 and R2 represent alkyl groups. The thiol-sulphoxides are preferably prepared by reacting a mercaptan RSH with ethylene chlorhydrin, if desired in the presence of an alkali, halogenating the remelting hydroxy ethyl sulphide to the corresponding halo ethyl sulphide with, for example, thionyl chloride and thereafter, before or after oxidation to the corresponding sulphoxide, reacting with thiourea and hydrolysing. Alternatively, the hydroxy ethyl sulphide made as above is converted into the corresponding vinyl sulphide by removal of the elements of water, for example with the aid of solid KOH, the vinyl sulphide is oxidised to the sulphoxide and the latter is then reacted with an alkali metal bisulphide yielding the alkali metal of the desired thiol sulphoxide which is acidified to liberate the free mercaptan. Finally, the thiol sulphoxides may be prepared by synthesising the halo-ethyl sulphide as above, oxidising the sulphide to the sulphoxide and then reacting with an alkali hydro sulphide, for example alcoholic NaSH. The oxidation may be effected with H2O2 in acetone or acetic acid. Examples (1)-(4) describe the preparation by one or other of the above methods using thiourea of ethyl b -thiol ethyl sulphoxide, n-butyl b -thiol ethyl sulphoxide and b -naphthyl b -thiol ethyl sulphoxide and thiol sulphoxides wherein R represents methyl, n-propyl, iso propyl, iso butyl or phenyl may be obtained similarly. In Example 5, ethyl-b -thiol ethyl sulphoxide is reacted with sodium metal and the resulting sodium mercaptide reacted in benzene with diethyl phosphorochloridate and the thiolo phosphate (R, R1 and R2=ethyl) so formed is isolated and purified by treatment with a mixture of charcoal and kieselguhr. Reference has been directed by the Comptroller to Specifications 742,769 and 795,860.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2287357A GB863370A (en) | 1957-07-19 | 1957-07-19 | New thiol-sulphoxides, their preparation and use as intermediates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2287357A GB863370A (en) | 1957-07-19 | 1957-07-19 | New thiol-sulphoxides, their preparation and use as intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB863370A true GB863370A (en) | 1961-03-22 |
Family
ID=10186408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2287357A Expired GB863370A (en) | 1957-07-19 | 1957-07-19 | New thiol-sulphoxides, their preparation and use as intermediates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB863370A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5463132A (en) * | 1990-08-24 | 1995-10-31 | Institut Francais Du Petrole | Process for the preparation of phosphosulfide compounds useful as oil lubricants |
| CN103664715A (en) * | 2013-12-17 | 2014-03-26 | 南京师范大学 | Method for synthesizing sulfoxide from thioether through catalytic oxidation |
-
1957
- 1957-07-19 GB GB2287357A patent/GB863370A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5463132A (en) * | 1990-08-24 | 1995-10-31 | Institut Francais Du Petrole | Process for the preparation of phosphosulfide compounds useful as oil lubricants |
| CN103664715A (en) * | 2013-12-17 | 2014-03-26 | 南京师范大学 | Method for synthesizing sulfoxide from thioether through catalytic oxidation |
| CN103664715B (en) * | 2013-12-17 | 2016-06-15 | 南京师范大学 | The method of thioether through catalytic oxidation synthesis sulfoxide |
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