Acetic Anhydride → HCID 54269052, compound

HRID 745094Notes

Reaction equation

HRID 745094 reaction equation
[OH:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:32]([O:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 73629978HCID 73629978, compound

Product 1

HCID 54269052HCID 54269052, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-hydroxyimino-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.06 g) in acetic anhydride (10 ml) and pyridine (10 ml) is stirred at room temperature overnight. After completion of the reaction, the reaction solution is concentrated. To the resulting residue is added water and the mixture is extracted with dichloromethane. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=80:1), and recrystallized from ethanol/petroleum ether to give 5-acetyloxyimino-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.75 g) as colorless prisms, m.p. 142°-144° C.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution is concentrated
  3. additionTo the resulting residue is added water
  4. extractionthe mixture is extracted with dichloromethane
  5. washThe extract is washed with saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=80:1)
  9. customrecrystallized from ethanol/petroleum ether

Sources & evidence

ORD record
ord-8b74d50c3cf444c5a7b15baddfced036
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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