Patent US5842014A successfully refreshed from Google Patents.
US4153607A
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Process for the production of 4,5-disubstituted thiazoles
Assignee: BASF SE
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Filing: 1978-02-24
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Granted: 1979-05-08
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Expires: 1998-02-24
Abstract
Abstract 4,5-Disubstituted thiazoles are manufactured by reacting 4-amino-5-cyano-thiazoles with hydrogen sulfide in the presence of basic compounds, followed by dehydrogenating cyclization. The new 3-amino-thiazolo-(4,5-c)-isothiazoles I, 4-amino-5-thiocarbamidothiazoles III and 4,5-disubstituted thiazoles IV obtainable by the process of the invention are valuable intermediates for the manufacture of azo dyes and of crop protection agents.
Inventors
- 👤 Heinz Eilingsfeld
- 👤 Guenther Seybold
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 05:54
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/56
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
203 words
A process for the manufacture of a 3-amino-thiazolo-(4,5-c)-isothiazole of the formula ##STR15## where R 1 is hydrogen, alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 12 carbon atoms, phenyl, ##STR16## the individual radicals R 2 are identical or different and each is alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 12 carbon atoms or phenyl, the two radicals R 2 present as substituents of the nitrogen atom may also form, together with the latter, a 5-membered or 6-membered heterocyclic ring, which in addition to the nitrogen atom may also contain an oxygen atom, wherein the above radicals and rings may in addition be substituted by alkyl or alkoxy each of 1 to 4 carbon atoms, which process comprises: in a first step, reacting a 4-amino-5-cyanothiazole of the formula ##STR17## where R 1 has the above meaning, with hydrogen sulfide in the presence of at least one basic compound selected from the group consisting of alkaline earth metal compounds, alkali metal compounds, ammonium compounds, tertiary amines, primary amines or secondary amines, and, in a second stage, cyclizing the resulting 4-amino-5-thiocarbamido-thiazole of the formula ##STR18## where R 1 has the above meaning, in the presence of a dehydrogenating agent.
Claim 2
Dependent Claim
203 words
A process for the manufacture of a 3-amino-thiazolo-(4,5-c)-isothiazole of the formula ##STR15## where R 1 is hydrogen, alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 12 carbon atoms, phenyl, ##STR16## the individual radicals R 2 are identical or different and each is alkyl of 1 to 6 carbon atoms, aralkyl of 7 to 12 carbon atoms or phenyl, the two radicals R 2 present as substituents of the nitrogen atom may also form, together with the latter, a 5-membered or 6-membered heterocyclic ring, which in addition to the nitrogen atom may also contain an oxygen atom, wherein the above radicals and rings may in addition be substituted by alkyl or alkoxy each of 1 to 4 carbon atoms, which process comprises: in a first step, reacting a 4-amino-5-cyanothiazole of the formula ##STR17## where R 1 has the above meaning, with hydrogen sulfide in the presence of at least one basic compound selected from the group consisting of alkaline earth metal compounds, alkali metal compounds, ammonium compounds, tertiary amines, primary amines or secondary amines, and, in a second stage, cyclizing the resulting 4-amino-5-thiocarbamido-thiazole of the formula ##STR18## where R 1 has the above meaning, in the presence of a dehydrogenating agent.
Claim 3
Dependent Claim
33 words
A process as set forth in claim 1, wherein the first step of the reaction is carried out with from 1 to 3 moles of hydrogen sulfide per mole of starting material II.
Claim 4
Dependent Claim
30 words
A process as set forth in claim 1, wherein the first step of the reaction is carried out with sodium sulfide, potassium sulfide, ammonium bisulfide, sodium bisulfide or potassium bisulfide.
Claim 5
Dependent Claim
23 words
A process as set forth in claim 1, wherein both steps of the reaction are carried out at from 0° to 150° C.
Claim 6
Dependent Claim
23 words
A process as set forth in claim 1, wherein both steps of the reaction are carried out at from 15° to 70° C.
Claim 7
Dependent Claim
48 words
A process as set forth in claim 1, wherein both steps of the reaction are carried out in the presence of solvents which are inert under the reaction conditions and are used in an amount of from 400 to 10,000 percent by weight, based on starting material II.
Claim 8
Dependent Claim
41 words
A process as set forth in claim 1, wherein the first step of the reaction is carried out in the presence of a basic compound used in an amount of from 0.003 to 1 equivalent per mole of starting material II.
Claim 9
Dependent Claim
33 words
A process as set forth in claim 1, wherein the second step of the reaction is carried out with from 1 to 3 equivalents of dehydrogenating agent per mole of starting material II.
Claim 10
Dependent Claim
43 words
A process as set forth in claim 1, wherein the second step of the reaction is carried out with phosphorus pentabromide, phosphorus pentachloride, sulfuryl chloride, sulfuryl bromide, chlorine, bromine, iodine, tert.-butyl hypochlorite, tert.-butyl hypobromite, sodium hypochlorite, potassium hypochlorite, sodium hypobromite or potassium hypobromite.
Claim 11
Dependent Claim
40 words
A process as set forth in claim 1, wherein the second step of the reaction is carried out with oxygen as the oxidizing agent, used in a ratio of from 0.05 to 2 moles per mole of starting material II.
Claim 12
Dependent Claim
21 words
A process as set forth in claim 1, wherein the second step of the reaction is carried out with hydrogen peroxide.
Claim 13
Dependent Claim
29 words
A process as set forth in claim 1, wherein the second step of the reaction is carried out with sulfuric acid in combination with halogens, halides or acid chlorides.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-07 | 1982-11-06 | 1983-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-07 | 1986-11-06 | 1987-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-07 | 1990-11-06 | 1991-05-08 | $7700.00 | Window Closed / Lapsed |