HCID 86623272, compound → HCID 10407515, compound

HRID 1787878Notes

Reaction equation

HRID 1787878 reaction equation
FC(F)(F)C([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:19][C:20]2[C:25]([F:26])=[C:24]([F:27])[C:23]([C:28]([F:31])([F:30])[F:29])=[C:22]([F:32])[C:21]=2[F:33])C(=O)C(F)(F)F)=[CH:8][C:7]=1[C:34](=[O:36])[NH2:35])=O>CO.O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:19][C:20]2[C:21]([F:33])=[C:22]([F:32])[C:23]([C:28]([F:31])([F:30])[F:29])=[C:24]([F:27])[C:25]=2[F:26])=[CH:8][C:7]=1[C:34]([NH2:35])=[O:36]

Participants

4

Reactant 1

HCID 86623272HCID 86623272, compound

Product 1

HCID 10407515HCID 10407515, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-carbamoyl-4-[2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl-(2,2,2-trifluoroacetyl)amino]phenyl trifluoroacetate (300 mg, 0.52 mmole) in methanol (8 ml) and water (3 ml) was added c-HCl (2.0 ml) at 40° C. under a nitrogen atmosphere. After the reaction mixture was stirred for 24 hr, the organic solvent was removed in vacuo. The residue was extracted with ethyl acetate (20 ml×3). The organic layer was washed with water and then dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was recrystallized from methylene chloride/hexane (1:10) to give 120 mg (60% yield) of 2-hydroxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzamide as a white solid.

Workup

  1. customthe organic solvent was removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate (20 ml×3)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue was recrystallized from methylene chloride/hexane (1:10)

Sources & evidence

ORD record
ord-66851f08c5224104813f8dba4d0abb62
Source dataset
uspto-grants-2009_03
Patent number
US07511074B2

Reaction notes

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