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

HRID 464544

Reaction equation

HRID 464544 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18]N(C)C)[CH2:8][N:9]=[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:27])C.[CH:29]([NH2:31])=[NH:30]>C(N)=N>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:31]=[CH:29][N:30]=[CH:18][C:7]=3[CH2:8][N+:9]([O-:27])=[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 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

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 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-515f29ae85514685a4eb136cb16f9f91
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Linked notes

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