Triethylamine → HCID 67625330, compound

HRID 1938303Notes

Reaction equation

HRID 1938303 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:19][C:20]1[CH:42]=[CH:41][C:23]([C:24]([N:26]2[CH2:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[CH2:29][C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[O:25])=[CH:22][CH:21]=1>O>[CH:37]1[C:28]2[CH2:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[CH2:32][N:26]([C:24]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:2]=4[Cl:1])=[CH:42][CH:41]=3)=[O:25])[C:27]=2[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179442,3-Dichlorobenzoyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 67625330HCID 67625330, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 301.6 mg of 2,3-dichlorobenzoyl chloride and 145 mg of triethylamine is stirred while 314 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz-[b,e]azepine is added. Stirring is continued for 2 hours. Water is added and the organic layer washed with 1N HCl, water, 1M NaHCO3 and water then dried over Na2SO4. The organic layer is passed through a pad of hydrous magnesium silicate and hexane added to the filtrate at the boil to give 0.32 g of the desired product as a crystalline solid, m.p. 225°-230° C.

Workup

  1. additionis added
  2. washthe organic layer washed with 1N HCl, water, 1M NaHCO3 and water
  3. dry with materialthen dried over Na2SO4
  4. additionadded to the filtrate at the boil

Sources & evidence

ORD record
ord-2452d5a713694198909f178a22d1d10c
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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