o-Benzylbenzoic acid → 2-Benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-benzamide

HRID 1358612Notes

Reaction equation

HRID 1358612 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:29][C:30]([F:44])([F:43])[C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:34][NH2:35]>O1CCCC1>[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:35][CH2:34][C:33]1[CH:36]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:38]=[C:31]([C:30]([F:29])([F:43])[F:44])[CH:32]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11924o-Benzylbenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 5210993,5-Bis(trifluoromethyl)benzylamine

Product 1

HCID 98243732-Benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-benzamideYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 255 mg (1.2 mmol) 2-benzylbenzoic acid in 1.5 ml tetrahydrofuran at 0° C. were added 195 mg (1.2 mmol) 1,1′-carbonyldiimidazole. After stirring for 2.5 h at room temperature, a solution of 243 mg (1.0 mmol) 3,5 bis(trifluoromethyl)benzylamine in 0.5 ml tetrahydrofuran was added and stirring was continued overnight. The solvent was removed in vacuo and the residue was purified by flash chromatography to give 210 mg (49%) of the title compound as white crystals.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d1857aea3757476a9b3976ae0995923a
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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