Water → HCID 67625966, compound

HRID 362417Notes

Reaction equation

HRID 362417 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-fluorobenzoyl 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 over 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. dry with materialthen dried over Na2SO4
  4. customThe desired product crystallizes from methylene chloride

Sources & evidence

ORD record
ord-a394a2b70fde46aebcb9017b5aecabb7
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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