2,6-Dichlorobenzoyl chloride → HCID 67623947, compound

HRID 1938302Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].C(N(CC)C(C)C)(C)C.[NH2:21][C:22]1[CH:44]=[CH:43][C:25]([C:26]([N:28]2[CH2:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[CH2:31][C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]2=3)=[O:27])=[CH:24][CH:23]=1>C1(C)C(C)=CC=CC=1>[CH:39]1[C:30]2[CH2:31][C:32]3[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=3[CH2:34][N:28]([C:26]([C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:4](=[O:5])[C:3]4[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=4[Cl:11])=[CH:44][CH:43]=3)=[O:27])[C:29]=2[CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 335 mg of 2,6-dichlorobenzoyl chloride and 258 mg of N,N-diisopropylethylamine is stirred in 2 ml of xylene while 314 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine is added. The reactants are refluxed in an oil bath at 110° C. for 18 hours. The xylene is evaporated in vacuo to a residue which is partitioned between methylene chloride and water. The organic layer is separated, washed with 1N HCl, 1M NaHCO3, and brine. The organic layer is dried with Na2SO4 and passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 370 mg of the desired product as a crystalline solid, m.p. 257°-259° C.

Workup

additionis added
customThe xylene is evaporated in vacuo to a residue which
customis partitioned between methylene chloride and water
customThe organic layer is separated
washwashed with 1N HCl, 1M NaHCO3, and brine
dry with materialThe organic layer is dried with Na2SO4
additionHexane is added to the filtrate at the boil

Sources & evidence

ORD record: ord-9206881f8b934744bc716b2a3c129162
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693635

Reaction notes

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