Hydrochloric Acid → 5-Chloro-2-hydroxy-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl)-methyl)benzamide

HRID 644453Notes

Reaction equation

HRID 644453 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:8]=1[C:9]([NH:11][CH2:12][C:13](=[O:29])[NH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)=[O:10])(=O)C.Cl>CO.O1CCCC1>[Cl:34][C:31]1[CH:32]=[CH:33][C:7]([OH:6])=[C:8]([CH:30]=1)[C:9]([NH:11][CH2:12][C:13](=[O:29])[NH:14][C:15]1[CH:16]=[C:17]([C:25]([F:27])([F:28])[F:26])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 230699552-acetoxy-5-chloro-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl)methyl)benzamide

Product 1

HCID 103885485-Chloro-2-hydroxy-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl)-methyl)benzamideYield 63.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

5N Aqueous sodium hydroxide (0.1 mL) was added to a solution of 2-acetoxy-5-chloro-N-({[3,5-bis(trifluoromethyl)phenyl]carbamoyl}methyl)benzamide (83.7 mg, 0.17 mmol) in methanol/tetrahydrofuran (2 mL+1 mL), and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) and washed with n-hexane under suspension to give the title compound (47.7 mg, 63.7%) as a white crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)
  6. washwashed with n-hexane under suspension

Sources & evidence

ORD record
ord-b6f8d379c38b4bfa8575aa4734836663
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

Loading…