4-(Trifluoromethyl)thiobenzamide → HCID 69055671, compound

HRID 854521Notes

Reaction equation

HRID 854521 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=O)[CH:6](Br)[CH2:7][CH2:8][CH3:9].[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>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]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:6]=1[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 71356077Methyl 4-bromo-3-oxoheptanoate

Product 1

HCID 69055671HCID 69055671, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-3-oxo-heptanoic acid methyl ester (6.0 g, 25.0 mmol) is dissolved into denatured ethanol (100 mL) and para-trifluoromethyl thiobenzamide (5.0 g, 24.4 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 add further purified using flash column chromatography (10% EtOAc/Hexanes) to yield pure [[5-Propyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid methyl ester (8.66 g, 24.2 mmol) or 98% 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. additionadd further
  10. custompurified

Sources & evidence

ORD record
ord-0722eb6c494a4ff0a99beeabfc927a2b
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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