Acetic Anhydride → 9-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-5-ol acetate

HRID 464537Notes

Reaction equation

HRID 464537 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:22]=[CH:21][N:20]=[CH:19][C:7]=3[CH2:8][N+:9]([O-])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[C:25]([O:28]C(=O)C)(=[O:27])[CH3:26]>>[C:25]([O:28][CH:8]1[C:7]2[CH:19]=[N:20][CH:21]=[N:22][C:6]=2[C:5]2[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][C:4]=2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[N:9]1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 132023249-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide

Product 1

HCID 132023259-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-5-ol acetate

Procedure

A mixture of 3 g (8 mmole) of 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide and 50 ml of acetic anhydride was heated on the steam bath for 22 hrs. The reaction mixture was concentrated at reduced pressure to dryness and the residue was crystallized from a mixture of methylene chloride and ether to give a product of mp 211°-212° C. Recrystallization from a mixture of methylene chloride and ether gave the pure product as colorless prisms, mp 211°-212° C.

Workup

  1. temperaturewas heated on the steam bath for 22 hrs
  2. concentrationThe reaction mixture was concentrated at reduced pressure to dryness
  3. customthe residue was crystallized from a mixture of methylene chloride and ether
  4. customto give a product of mp 211°-212° C
  5. customRecrystallization
  6. additionfrom a mixture of methylene chloride and ether

Sources & evidence

ORD record
ord-0694608a5f76454d9ada48de186ac4b3
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

Loading…