Pyridine → 5-Benzoylamino-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide

HRID 2384385Notes

Reaction equation

HRID 2384385 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)=[O:8].N1C=CC=CC=1.O1CCCC1.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O>[C:37]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)=[O:8])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 10406441HCID 10406441, compound

Product 1

HCID 100502785-Benzoylamino-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamideYield 25.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon atmosphere, a mixture of 5-amino-N-[3,5-bis(trifluoromethyl)-phenyl]-2-hydroxybenzamide (364 mg, 1 mmol), pyridine (95 mg, 1.2 mmol) and tetrahydrofuran (10 mL) was cooled on ice. Benzoyl chloride (155 mg, 1.1 mmol) was added, and the mixture was stirred for 1 hour. The reaction mixture was poured into water 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 (n-hexane:ethyl acetate=4:1) to give the title compound (121 mg, 25.7%) as a white solid.

Workup

  1. temperaturewas cooled on ice
  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 (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9b0ed102d5f44b34ad3a287402fb024f
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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