Water → 7-Benzothiazolecarboxylic acid

HRID 560314Notes

Reaction equation

HRID 560314 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. HCl. After 30 min the precipitate is filtered off, washed with water and dried in vacuo to give the desired product.

Workup

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

Sources & evidence

ORD record
ord-6fd7288e3c5d487dbfa3fa6a044b37cd
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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