Hydrogen Bromide → 2-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid

HRID 1498905Notes

Reaction equation

HRID 1498905 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16]CC)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[C:4]([O:19][CH3:20])[CH:3]=1.[OH-].[Na+].Br>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 68642456Ethyl 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylate

Product 1

HCID 686420482-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylate (4.83 g, 15.5 mmol) prepared in the Step 7-1-3 was suspended in ethanol (30 ml), 1 mol/l of sodium hydroxide (30 ml) was added thereto, and the mixture was heated under reflux for 1.5 hours. After being allowed to cool, the mixture was neutralized with hydrobromic acid, then separated by filtration and washed with water. The washed product was subjected to through circulation drying to give the title compound (4.28 g, 97%) as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool
  4. customseparated by filtration
  5. washwashed with water
  6. customdrying

Sources & evidence

ORD record
ord-be7a5f609fa6480c945041ae81283da5
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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