4-(Trifluoromethyl)thiobenzamide → HCID 69055671, compound

HRID 490708Notes

Reaction equation

HRID 490708 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 washes 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-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. customfurther purified

Sources & evidence

ORD record
ord-1f4b3dd533d043e99d036a292f2e4b24
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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