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Triethylamine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]-2,3,5-trichlorobenzamide

HRID 1288994
Notes
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Reaction equation

HRID 1288994 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:20][C:21]1[CH:43]=[CH:42][C:24]([C:25]([N:27]2[CH2:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[CH2:30][C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]2=3)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH:38]1[C:29]2[CH2:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH2:33][N:27]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:4](=[O:5])[C:3]4[CH:7]=[C:8]([Cl:12])[CH:9]=[C:10]([Cl:11])[C:2]=4[Cl:1])=[CH:43][CH:42]=3)=[O:26])[C:28]=2[CH:41]=[CH:40][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130111162,3,5-Trichlorobenzoyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 67624157N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]-2,3,5-trichlorobenzamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A mixture of 366 mg of 2,3,5-trichlorobenzoyl chloride and 151 mg of triethylamine in 2 ml of methylene chloride is stirred while 314 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine in 5 ml of methylene chloride is added. Stirring is continued for 1.5 hours. The reaction mixture is partitioned with water and the organic layer is washed with 2N HCl. water, 0.5N NaOH and brine. The organic layer is dried with Na2 SO4 and passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 0.52 g of white solid residue which is purified by column chromatography on silica gel by elution with 2:1 hexane-ethyl acetate to give 120 mg of the desired product as a crystalline solid, m.p. 225°-230° C.

Workup

  1. additionis added
  2. customThe reaction mixture is partitioned with water
  3. washthe organic layer is washed with 2N HCl
  4. customThe organic layer is dried with Na2 SO4
  5. additionHexane is added to the filtrate at the boil

Sources & evidence

ORD record
ord-4ba1b7ffab524b1588a665f2626de700
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05747487

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes