Water → HCID 67625966, compound

HRID 355918Notes

Reaction equation

HRID 355918 reaction equation
C[C:2]1([CH:10]=[CH:9][CH:8]=[CH:7][CH:6]1[F:11])C(Cl)=O.C(N([CH2:17][CH3:18])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.[OH2:43]>>[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:7](=[O:43])[C:8]4[CH:9]=[CH:10][CH:2]=[C:6]([F:11])[C:17]=4[CH3:18])=[CH:42][CH:41]=3)=[O:25])[C:27]=2[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineHCID 86751687HCID 86751687, compound

Product 1

HCID 67625966HCID 67625966, compound

Procedure

A mixture of 248.5 mg of 1-methyl-2-fluoro-benzoyl chloride and 145 mg of triethylamine is stirred while 376.8 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine is added. Stirring is continued for 3 hours. Water is added and the organic layer washed with 1N HCl, water, 1M NaHCO3 and water then dried oyer Na2SO4. The organic layer is passed through a pad of hydrous magnesium silicate. The desired product crystallizes from methylene chloride to give 0.417 g of the desired product, m.p. 167°-170° C.

Workup

  1. additionis added
  2. washthe organic layer washed with 1N HCl, water, 1M NaHCO3 and water
  3. customThe desired product crystallizes from methylene chloride

Sources & evidence

ORD record
ord-c4edb90d74324edeaae008e1d038e427
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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