4-(Trifluoromethyl)thiobenzamide → HCID 69056840, compound

HRID 860617Notes

Reaction equation

HRID 860617 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6](=O)[CH:7](Br)[CH2:8][CH3:9])[CH3:2].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[S:20])=[CH:17][CH:16]=1>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:21]=[C:19]([C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:24])([F:13])[F:25])=[CH:23][CH:22]=2)[S:20][C:7]=1[CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 1278044452851-15-7

Product 1

HCID 69056840HCID 69056840, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-3-oxo-hexanoic acid ethyl ester (4.68 g, 20.98 mmol) is dissolved into denatured ethanol (100 mL) and para-trifluoromethyl thiobenzamide (4.31 g, 21 mmol) is added in one portion. The reaction is purged of air and flushed with nitrogen then heated to reflux. The reaction is monitored by TLC and HPLC and when complete, the reaction is allowed to cool to room temperature. The solvent is removed and the reaction is diluted with ethyl acetate (200 mL), followed by ishes with saturated sodium bicarbonate solution, water, and brine. The ethyl acetate solution is dried over anhydrous sodium sulfate, then concentrated and further purified using flash column chromatography (10% EtOAc/Hexanes) to yield pure [5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (5.09 g, 14.82 mmol) or 71% yield.

Workup

  1. additionis added in one portion
  2. customThe reaction is purged of air
  3. customflushed with nitrogen
  4. temperaturethen heated to reflux
  5. customThe solvent is removed
  6. additionthe reaction is diluted with ethyl acetate (200 mL)
  7. dry with materialThe ethyl acetate solution is dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customfurther purified

Sources & evidence

ORD record
ord-39cae151ca5a4169a7fed716e10688eb
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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