Triethylamine → N-[4-[(Dibenz[b,f][1,4]thiazepin-10(11H)yl)carbonyl]phenyl]-2-chlorobenzamide

HRID 1289011Notes

Reaction equation

HRID 1289011 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:34]=[CH:33][C:15]([C:16]([N:18]2[CH2:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21][C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]2=3)=[O:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:25]1[C:23]2[CH2:24][N:18]([C:16]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[Cl:1])=[CH:34][CH:33]=3)=[O:17])[C:19]3[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=3[S:21][C:22]=2[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 5423000210,11-Dihydro-10-(4-aminobenzoyl)dibenz[b,f][1,4]thiazepine

Product 1

HCID 67624707N-[4-[(Dibenz[b,f][1,4]thiazepin-10(11H)yl)carbonyl]phenyl]-2-chlorobenzamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 385 mg of 2-chloro-benzoyl chloride in 6 ml of methylene chloride at 0 ° C. is added 0.6 g of 10-(4-aminobenzoyl)-10,11-dihydrodibenz[b,f]-[1,4]thiazepine followed by 0.375 ml of triethylamine. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is washed with 20 ml of water, 1N HCl, 1N Na2CO3, water and dried over MgSO4. The filtrate is evaporated in vacuo to give 0.7 g of yellowish solid which is purified by silica gel chromatography on thick layer plates by elution with 1:1 ethyl acetate-hexane to give 0.3 g of the desired product, m.p. 116°-119 ° C.

Workup

  1. washThe reaction mixture is washed with 20 ml of water, 1N HCl, 1N Na2CO3, water
  2. dry with materialdried over MgSO4
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-41f32c5643d648dbb045d7d6f041d1b3
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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