6,11-Dihydro-5H-dibenz[b,e]azepine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-2-chlorophenyl]-2-methyl-3-fluorobenzamide

HRID 355925Notes

Reaction equation

HRID 355925 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[CH3:25][C:26]1[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:27]=1[C:28]([NH:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][C:32]=1[Cl:40])=[O:29]>C(Cl)Cl>[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:35]([C:34]3[CH:38]=[CH:39][C:31]([NH:30][C:28](=[O:29])[C:27]4[CH:41]=[CH:42][CH:43]=[C:44]([F:45])[C:26]=4[CH3:25])=[C:32]([Cl:40])[CH:33]=3)=[O:36])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 81531DiisopropylethylamineHCID 542731774-[(2-Methyl-3-fluorobenzoyl)amino)-3-chlorobenzoyl chloride

Product 1

HCID 67624513N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-2-chlorophenyl]-2-methyl-3-fluorobenzamideYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of 6,11-dihydro-5H-dibenz-[b,e]azepine, 0.80 g of N,N-diisopropylethylamine and 2.01 g of 4-[(2-methyl-3-fluorobenzoyl)amino]-3-chlorobenzoyl chloride in 100 ml of methylene chloride is stirred at room temperature for 18 hours. The reaction mixture is washed with water, saturated NaHCO3, dried (Na2SO4) and passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 1.79 g of the desired product as a crystalline solid, m.p. 254°-256° C.

Workup

  1. washThe reaction mixture is washed with water, saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. additionHexane is added to the filtrate at the boil

Sources & evidence

ORD record
ord-8846b14a1afc472faadbb84c274d6792
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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