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

HRID 2293284Notes

Reaction equation

HRID 2293284 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, 1 N HCl, 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, 1 N HCl, 1N Na2CO3, water
  2. dry with materialdried over MgSO4
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-10136550f8e542e1827723df9f032423
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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