Potassium Hydroxide → 2-(4-Chloroanilino)-1,3-thiazole-5-carboxylic acid

HRID 2222199Notes

Reaction equation

HRID 2222199 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[K+]>C1COCC1.CO>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 34178007Ethyl 2-(4-chloroanilino)-1,3-thiazole-5-carboxylate

Product 1

HCID 341779822-(4-Chloroanilino)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3.0 g (11.1 mmol) 2-(4-Chloro-phenylamino)-thiazole-5-carboxylic acid ethyl ester and 6.7 ml 5M KOH in 50 ml THF and 10 ml MeOH was heated to 50° C. for 4 h and subsequently concentrated. The residue was taken up in water, acidified with acetic acid and extracted with ethyl acetat. The combined organic layers were washed with water, dried with MgSO4 and evaporated. The residue was recrystallised from ethyl acetate to obrain 2.0 g (70%) of the title compound as white crystals. (m/e): 254.9 (M+H+, 100%)

Workup

  1. concentrationsubsequently concentrated
  2. extractionextracted with ethyl acetat
  3. washThe combined organic layers were washed with water
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-00cbbde3cc5e4cd9bd94e90c32a1143f
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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