US4612378A
Expired / Lapsed
US
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Process for the preparation of β-(benzothiazolylthio)- and β-(benzimidazolylthio-carboxylic acids
Assignee: HALOX A DIVISION OF HAMMOND GROUP Inc
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Filing: 1984-05-14
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Granted: 1986-09-16
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Expires: 2004-05-14
Abstract
Abstract The reaction of 2-mercapto-benzothiazole or -benzimidazole with α,β-unsaturated carboxylic acids in a strongly acid reaction medium gives compounds of the formula I ##STR1## in which X is sulfur or NH, each radical R independently of one another is H, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulfonyl, phenyl, alkylphenyl, phenylalkyl, cycloalkyl, halogen, NO 2 , CN, COOH, COOalkyl, OH or an amino or carbamyl group and R 1 , R 2 and R 3 independently of one another are H, alkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl, carboxyl or unsubstituted or substituted aryl or aralkyl, or R 1 and R 2 together are straight-chain or branched alkylene, which can be substituted by 1 or 2 carboxyl groups.
Inventors
- 👤 Hans Bosshard
- 👤 Hans Greuter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:16
CPC Classifications
C; C09; C09D; C09D5/00; C09D5/08; C09D5/082; C09D5/086; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
149 words
A process for the preparation of a compound of the formula I ##STR5## in which X is sulfur or NH, each radical R is the same or different from each other radical R and is hydrogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulfonyl, phenyl, alkylphenyl, phenylalkyl, cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COOalkyl, --OH or a primary, secondary or tertiary amino or carbamyl group and R 1 , R 2 and R 3 are all the same or different and are hydrogen, alkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl, carboxyl or unsubstituted or substituted aryl or aralkyl, or R 1 and R 2 together are a direct bond or straight-chain or branched alkylene, which can be substituted by 1 or 2 carboxyl groups, by reaction of a mercaptan of the formula II ##STR6## with an unsaturated carboxylic acid of the formula III ##STR7## or an anhydride thereof, in a strongly acid medium.
Claim 2
Dependent Claim
149 words
A process for the preparation of a compound of the formula I ##STR5## in which X is sulfur or NH, each radical R is the same or different from each other radical R and is hydrogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulfonyl, phenyl, alkylphenyl, phenylalkyl, cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COOalkyl, --OH or a primary, secondary or tertiary amino or carbamyl group and R 1 , R 2 and R 3 are all the same or different and are hydrogen, alkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl, carboxyl or unsubstituted or substituted aryl or aralkyl, or R 1 and R 2 together are a direct bond or straight-chain or branched alkylene, which can be substituted by 1 or 2 carboxyl groups, by reaction of a mercaptan of the formula II ##STR6## with an unsaturated carboxylic acid of the formula III ##STR7## or an anhydride thereof, in a strongly acid medium.
Claim 3
Dependent Claim
21 words
A process according to claim 1, wherein the reaction medium is the aqueous or organic-aqueous solution of a strong proton acid.
Claim 4
Dependent Claim
18 words
A process according to claim 2, wherein the reaction medium is 60-90% sulfuric acid or 25-38% hydrochloric acid.
Claim 5
Dependent Claim
21 words
A process according to claim 1, wherein the reaction is carried out at a temperature of 0° C. to 100° C.
Claim 6
Dependent Claim
26 words
A process according to claim 1, wherein a mercaptan of the formula II in which at least two of the substituents R are hydrogen is used.
Claim 7
Dependent Claim
38 words
A process according to claim 5, wherein one of the radicals R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, --COOH or an amino group and the other three radicals R are hydrogen.
Claim 8
Dependent Claim
20 words
A process according to claim 1, wherein a compound of the formula II in which X is sulfur is used.
Claim 9
Dependent Claim
57 words
A process according to claim 1, wherein a carboxylic acid of the formula III in which R 1 , R 2 and R 3 are all the same or different and are hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -carboxyalkyl, carboxyl or phenyl, or R 1 and R 2 together are tetramethylene is used.
Claim 10
Dependent Claim
34 words
A process according to claim 1, wherein a carboxylic acid of the formula III in which at least two of the substituents R 1 , R 2 and R 3 are hydrogen is used.
Claim 11
Dependent Claim
35 words
A process according to claim 1, wherein a carboxylic acid of the formula III in which R 3 is carboxyl or R 2 is carboxymethyl, or the cyclic anhydride of such a compound, is used.
Claim 12
Dependent Claim
26 words
A process according to claim 10, wherein a compound of the formula II is reacted with maleic acid or maleic anhydride in a strongly acid medium.
References Cited (Backward Citations)
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