Hydrogen Bromide → Benzothiazole-6-carboxylic acid

HRID 1498969Notes

Reaction equation

HRID 1498969 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12]CC)=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].Br>C(O)C>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 10512520Ethyl benzo[d]thiazole-6-carboxylate

Product 1

HCID 601670Benzothiazole-6-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl benzothiazole-6-carboxylate (1.30 g, 6.28 mmol) prepared in the Step 36-1-2 was suspended in ethanol (10 ml) and a 1 mol/L sodium hydroxide aqueous solution (10 ml), and the mixture was heated under reflux for 40 minutes. After the mixture was allowed to cool, concentrated hydrobromic acid was added to the mixture, and the resulting mixture was adjusted to pH 4. The precipitate was separated by filtration, washed with water, and then subjected to through circulation drying to give the title compound (1.10 g, 98%) as a light-brown powder.

Workup

  1. temperatureunder reflux for 40 minutes
  2. temperatureto cool
  3. customThe precipitate was separated by filtration
  4. washwashed with water
  5. customdrying

Sources & evidence

ORD record
ord-bcb865b48d1d43babfcd1070fbaed53a
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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