Triethylamine → N-[4-[(5,11-dihydro-10H-dibenz[b,e](1,4]diazepin-5-yl)carbonyl]phenyl]-2-methylbenzamide

HRID 1459383Notes

Reaction equation

HRID 1459383 reaction equation
[CH:1]1[C:11]2[CH2:10][NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:34]=[CH:33][CH:32]=[CH:31][C:18]=1[C:19]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)=[O:20].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:1]1[C:11]2[CH2:10][NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([C:26]([C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:19](=[O:20])[C:18]4[CH:31]=[CH:32][CH:33]=[CH:34][C:17]=4[CH3:16])=[CH:30][CH:29]=3)=[O:27])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Product 1

HCID 67624893N-[4-[(5,11-dihydro-10H-dibenz[b,e](1,4]diazepin-5-yl)carbonyl]phenyl]-2-methylbenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of 5,11-dihydro-10H-dibenz[b,e][1,4]diazepine 1.9 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride, 4 ml of triethylamine and 0.2 g of 4-(dimethylamino)pyridine in 60 ml of methylene chloride is stirred at room temperature for 18 hours. The reaction mixture is poured into ice water and the separated organic layer washed with 50 ml each of water, 2N HCl, water, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and the solvent removed to give a residue. The residue is chromatographed on a silica gel column using 1:4 ethyl acetate-hexane to give 1.8 g of the desired product as a solid, m.p. 68°-71° C.

Workup

  1. washthe separated organic layer washed with 50 ml each of water, 2N HCl, water, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent removed
  4. customto give a residue
  5. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f5d946314156416c9a9ff53d119b8298
Source dataset
uspto-grants-1998_12
Patent number
US05854236

Reaction notes

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