Formamidine acetate → 9-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide

HRID 1979590Notes

Reaction equation

HRID 1979590 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6](=O)[C:7](=[CH:19][N:20](C)[CH3:21])[CH2:8][N+:9]([O-:18])=[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(O)(=O)C.C(N)=[NH:31]>C(N)=N>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[N:31]=[CH:21][N:20]=[CH:19][C:7]=3[CH2:8][N+:9]([O-:18])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 731657308-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one 2-oxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 68047FormamidineSolvent

Procedure

A mixture of 0.4 g (1.1 mmol) of 8-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one 2-oxide and 1.0 g (9.6 mmol) of formamidine acetate in 20 ml of formamidine was heated on a steam bath for 7 hr. The mixture was poured over ice and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was triturated with ether to give an off-white solid, mp 215°-217° C.

Workup

  1. temperaturewas heated on a steam bath for 7 hr
  2. additionThe mixture was poured over ice
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was triturated with ether
  8. customto give an off-white solid, mp 215°-217° C.

Sources & evidence

ORD record
ord-55248d7af39c4880acb23ff0b6bcda6d
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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