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US4091037A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of alkylthiomethylphenols

Assignee: Bayer AG
•
Filing: 1977-03-31
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Granted: 1978-05-23
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Expires: 1997-03-31
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Abstract

Abstract A process for the preparation of an alkylthiomethylphenol of the formula ##STR1## COMPRISING REACTING A DIALKYLAMINOMETHYLPHENOL OF THE FORMULA ##STR2## WITH A THIOCARBOXYLIC ACID S-ester of the formula ##STR3## in which R 1 is optionally substituted alkyl with 1 to 12 carbon atoms or optionally substituted phenyl, R 2 and R 3 each independently is hydrogen, alkyl with 1 to 5 carbon atoms, halogen or nitro, or together form a benzene ring or cycloalkane ring with 3 to 5 carbon atoms which is fused to the phenyl ring, R 4 and R 5 each independently is alkyl with 1 to 6 carbon atoms, or together with the nitrogen atom form a five- or six-membered heterocyclic ring, R 6 is hydrogen or alkyl with 1 to 6 carbon atoms, and n is 1, 2 or 3. The process may be carried out in a solvent, advantageously at a temperature from about 100° to 150° C, at about normal pressure using phenol as a catalyst with about 0.9 to 1.5 moles of thiocarboxylic acid S-ester per mole of dialkylaminomethylphenol.

Inventors

  • 👤 Hermann Arold

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 23:40
CPC Classifications
C; C07; C07C; C07C319/00; C07C319/14

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 165 words
A process for the preparation of an alkylthiomethylphenol of the formula ##STR11## comprising reacting at a temperature of about 70° to 170° C an aminomethylphenol of the formula ##STR12## with a thiocarboxylic acid S-ester of the formula ##STR13## in which R 1 is alkyl with 1 to 12 carbon atoms or alkoxyalkyl with from 1 to 6 carbon atoms in each alkyl moiety, benzyl, phenyl or phenyl carrying at least one C 1-6 alkyl or halogen substituent, R 2 and R 3 each independently is hydrogen, alkyl with 1 to 5 carbon atoms, halogen or nitro, or together form a benzene ring or cycloalkane ring with 3 to 5 carbon atoms which is fused to the phenyl ring, R 4 and R 5 each independently is alkyl with 1 to 6 carbon atoms, or together with the nitrogen atom form a five or six-membered heterocyclic ring, R 6 is hydrogen or alkyl with 1 to 6 carbon atoms, and n is 1, 2 or 3.
Claim 2
Dependent Claim 165 words
A process for the preparation of an alkylthiomethylphenol of the formula ##STR11## comprising reacting at a temperature of about 70° to 170° C an aminomethylphenol of the formula ##STR12## with a thiocarboxylic acid S-ester of the formula ##STR13## in which R 1 is alkyl with 1 to 12 carbon atoms or alkoxyalkyl with from 1 to 6 carbon atoms in each alkyl moiety, benzyl, phenyl or phenyl carrying at least one C 1-6 alkyl or halogen substituent, R 2 and R 3 each independently is hydrogen, alkyl with 1 to 5 carbon atoms, halogen or nitro, or together form a benzene ring or cycloalkane ring with 3 to 5 carbon atoms which is fused to the phenyl ring, R 4 and R 5 each independently is alkyl with 1 to 6 carbon atoms, or together with the nitrogen atom form a five or six-membered heterocyclic ring, R 6 is hydrogen or alkyl with 1 to 6 carbon atoms, and n is 1, 2 or 3.
Claim 3
Dependent Claim 59 words
A process according to claim 1, in which R 1 is C 1 -C 6 alkyl, alkoxyalkyl with from 1 to 6 carbon atoms in each alkyl moiety, benzyl, phenyl or phenyl carrying at least one C 1-6 alkyl or halogen substituent, and R 2 and R 3 each independently is hydrogen, C 1 -C 4 alkyl or chlorine.
Claim 4
Dependent Claim 34 words
A process according to claim 1, in which R 4 and R 5 each independently is C 1 -C 4 alkyl or together are C 4 H 8 or C 5 H 10 .
Claim 5
Dependent Claim 16 words
A process according to claim 1, in which R 6 is C 1 -C 4 alkyl.
Claim 6
Dependent Claim 19 words
A process according to claim 1, in which the reaction is carried out in the presence of a solvent.
Claim 7
Dependent Claim 16 words
A process according to claim 1, in which the reaction is carried out under normal pressure.
Claim 8
Dependent Claim 18 words
A process according to claim 1, in which the reaction is carried out using phenol as a catalyst.
Claim 9
Dependent Claim 23 words
A process according to claim 1, in which about 0.5 to 3 moles of thiocarboxylic acid S-ester are employed per mole of aminomethylphenol.
Claim 10
Dependent Claim 45 words
A process according to claim 2, in which the reaction is carried out at a temperature from about 100° to 150° C, at about normal pressure, using phenol as a catalyst with about 0.9 to 1.5 moles of thiocarboxylic acid S-ester per mole of aminomethylphenol.

References Cited (Backward Citations)

US2417118A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-05-22 1981-11-21 1982-05-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-05-22 1985-11-21 1986-05-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-05-22 1989-11-21 1990-05-23 $7700.00 Window Closed / Lapsed

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