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

HRID 1957678Notes

Reaction equation

HRID 1957678 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:12][C:13]1[CH:35]=[CH:34][C:16]([C:17]([N:19]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[S:22][C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]2=3)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:26]1[C:24]2[CH2:25][N:19]([C:17]([C:16]3[CH:15]=[CH:14][C:13]([NH:12][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=4[Cl:1])=[CH:35][CH:34]=3)=[O:18])[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[S:22][C:23]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 5423000210,11-Dihydro-10-(4-aminobenzoyl)dibenz[b,f][1,4]thiazepine

Product 1

HCID 67625596N-[4-[(Dibenz[b,f] [1,4]thiazepin-10(11H)-yl)carbonyl]phenyl]-2,4-dichlorobenzamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 452 mg of 2,4-dichlorobenzoyl chloride in 6 ml of methylene chloride 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 HC1, 1N Na2CO3, water and dried over MgSO4. The filtrate is evaporated in vacuo to give 0.72 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 0.254 g of the desired product as ivory crystals, m.p. 112°-115° C.

Workup

  1. washThe reaction mixture is washed with 20 ml of water, 1N HC1, 1N Na2CO3, water
  2. dry with materialdried over MgSO4
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-204951329dda4e66a3c44c4553197924
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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