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

HRID 2186784Notes

Reaction equation

HRID 2186784 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-caf8671f44e4452797a0d35236aceaf0
Source dataset
uspto-grants-2002_06
Patent number
US06407111B1

Reaction notes

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