Acetic Acid → HCID 59594756, compound

HRID 2263382Notes

Reaction equation

HRID 2263382 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:19]([F:21])[F:20])=[O:5])C.[OH-].[Li+].C(O)(=O)C>O1CCCC1.O>[F:21][CH:19]([F:20])[C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 59594764HCID 59594764, compound

Product 1

HCID 59594756HCID 59594756, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.0 g 4-Difluoromethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester were dissolved in 90 ml tetrahydrofuran. A solution of 2.29 g lithium hydroxide dissolved in 30 ml water was added and the reaction mixture stirred at room temperature overnight. Concentrated acetic acid were added until a pH of ˜6 was attained, then the tetrahydrofuran was removed in vacuo. The residual aqueous phase was extracted three time with portions of 100 ml ethyl acetate. The combined organic layers were dried over MgSO4. Then the solvent was removed in vacuo to obtain 2.73 g 4-difluoromethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid as pale yellow solid.

Workup

  1. additionwas added
  2. customthe tetrahydrofuran was removed in vacuo
  3. extractionThe residual aqueous phase was extracted three time with portions of 100 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThen the solvent was removed in vacuo

Sources & evidence

ORD record
ord-1ae752207c444d01834a023715ed1533
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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