4-(Trifluoromethyl)thiobenzamide → 4-(3-Benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 2263374Notes

Reaction equation

HRID 2263374 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5](Cl)[C:6](=O)[CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[S:28])=[CH:25][CH:24]=1>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[S:28][C:27]([C:26]2[CH:25]=[CH:24][C:23]([C:22]([F:32])([F:21])[F:33])=[CH:31][CH:30]=2)=[N:29][C:6]=1[CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 592953986-Benzyloxy-2-chloro-3-oxo-hexanoic acid ethyl ester

Product 1

HCID 595947664-(3-Benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.15 g of 6-benzyloxy-2-chloro-3-oxo-hexanoic acid ethyl ester in 10 ml of ethanol was added 0.932 g of 4-(trifluoromethyl)thiobenzamide. The reaction mixture was refluxed overnight. The solvent was removed under reduced pressure. The resulting residue was taken into ethyl acetate, washed with water. The aqueous layer was separated and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 90/ethyl acetate 10) to give 1.15 g of 4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester as a colorless liquid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel (heptane 90/ethyl acetate 10)

Sources & evidence

ORD record
ord-85d0d2fc56d643b3b8706997f63d33f0
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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