Water → 7-Benzothiazolecarboxylic acid

HRID 882786Notes

Reaction equation

HRID 882786 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:15]2[S:14][CH:13]=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:6].C1COCC1.O>CO>[S:14]1[C:15]2[C:7]([C:5]([OH:6])=[O:4])=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]=[CH:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59316815Methyl benzo[d]thiazole-7-carboxylate

Product 1

HCID 450769847-Benzothiazolecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C. an aq. NaOH solution (50%, 6.0 mL) is added to a solution of benzothiazole-7-carboxylic acid methyl ester in a mixture of MeOH (39 mL), THF (11.7 mL) and water (3.0 mL). The mixture is stirred for 4 h and concentrated in vacuo. At 0° C. water (60 mL) is added and the mixture is made acidic (pH 5) by addition of conc. hydrochloric acid. After 30 min the precipitate is filtered off, washed with water and dried in vacuo to give the desired product. LC-MS: tR=0.77 min; [M+CH3CN+H]+=221.1.

Workup

  1. concentrationconcentrated in vacuo
  2. additionAt 0° C. water (60 mL) is added
  3. additionby addition of conc. hydrochloric acid
  4. filtrationAfter 30 min the precipitate is filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ad42f6e6d8aa4cde8e19911102d488ad
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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