Ethanol → 2-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamide

HRID 644412Notes

Reaction equation

HRID 644412 reaction equation
[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([NH2:39])(=[S:38])[CH3:37].C(=O)([O-])O.[Na+].C(O)C>O>[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32]2[N:39]=[C:36]([CH3:37])[S:38][CH:33]=2)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:25])[F:26])[CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 2723949ThioacetamideHCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

Product 1

HCID 178602912-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamideYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (280 mg, 0.5 mmol), thioacetamide (41 mg, 0.55 mmol), sodium hydrogen carbonate (50 mg, 0.6 mmol) and ethanol (15 mL) was refluxed for 1 hour. The reaction mixture was poured into water, neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (181 mg, 67.5%) as a white solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified by chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1e65ba8dc5a74bc48c03d026cf8b4ce7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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