Acetic Anhydride → 4-Methoxy-2-methyl-6-benzothiazolecarboxylic acid

HRID 1393681Notes

Reaction equation

HRID 1393681 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[SH:13].[C:14](OC(=O)C)(=O)[CH3:15]>O1CCCC1>[CH3:12][O:11][C:10]1[C:2]2[N:1]=[C:14]([CH3:15])[S:13][C:3]=2[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23091979HCID 23091979, compound

Product 1

HCID 230919804-Methoxy-2-methyl-6-benzothiazolecarboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Amino-3-mercapto-5-methoxybenzoic acid (500 mg) was dissolved in tetrahydrofuran (15 ml) and cooled at −78° C. Acetic anhydride (0.26 ml) was added thereto, and the mixture was warmed over 30 minutes to room temperature and stirred for 3 hours. The reaction mixture was concentrated under reduced pressure to give the title compound (550 mg, Y.:99%) as white crystals.

Workup

  1. temperaturethe mixture was warmed over 30 minutes to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66f11644510d4f7c9ee942f8108f7b10
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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