2-(Trifluoromethyl)benzoyl chloride → N-[4-((6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-trifluoromethylbenzamide

HRID 1288987Notes

Reaction equation

HRID 1288987 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C(N(CC)CC)C>[CH:19]1[C:10]2[CH2:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[CH2:14][N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=4[C:26]([F:25])([F:36])[F:37])=[CH:24][CH:23]=3)=[O:7])[C:9]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 67625470N-[4-((6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-trifluoromethylbenzamideYield 58.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described for Example 9, a mixture of 0.377 g (1,44 mmol) of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.15 g of triethylamine and 0.300 g (1,44 mmol) of 2-trifluoromethylbenzoyl chloride is stirred at room temperature for 2 hours and then washed with 1N HCl 1M NaHCO3, brine and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filtrate evaporated to give a solid. Crystallization from dichloromethanehexane gives 0.41 g of crystals, m.p. 191°-193° C.

Workup

  1. washwashed with 1N HCl 1M NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customthe filtrate evaporated
  4. customto give a solid
  5. customCrystallization from dichloromethanehexane

Sources & evidence

ORD record
ord-270677b127684701add0cb9cd8d267d3
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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