Tetrahydrofuran → 3-hydroxy-N-[4-(trifluoromethyl)phenyl]benzamide

HRID 2190418Notes

Reaction equation

HRID 2190418 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[O:12])[CH:6]=1)(=O)C.O1CCCC1.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=1)=[O:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67312322HCID 67312322, compound

Product 1

HCID 283922023-hydroxy-N-[4-(trifluoromethyl)phenyl]benzamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-({[4-(trifluoromethyl)phenyl]amino}carbonyl)phenyl acetate (27.7 g, 85.5 mmol) in methanol (100 mL)/tetrahydrofuran (100 mL) was added 8N aqueous sodium hydroxide solution (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hr and dried under reduced pressure to solidness. The residue was poured into dilute hydrochloric acid (pH=2) and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated with diethyl ether to give the title compound (21.7 g, 90%) as a white solid.

Workup

  1. temperaturecooling
  2. customdried under reduced pressure to solidness
  3. additionThe residue was poured into dilute hydrochloric acid (pH=2)
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-a274b20f85684ae28b37965e2c4af424
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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