Ammonium Hydroxide → 9-Chloro-7-(2-chlorophenyl)-5H-pyrimido(5,4-d)(2)benzazepine

HRID 464202Notes

Reaction equation

HRID 464202 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.P(Cl)(Cl)Cl.[OH-].[NH4+]>C(Cl)Cl>[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]=[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

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24387Phosphorus trichlorideHCID 132023249-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide

Product 1

HCID 1317369-Chloro-7-(2-chlorophenyl)-5H-pyrimido(5,4-d)(2)benzazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.5 g (1.3 mmol) of 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide and 1.0 ml (10 mmol) of phosphorous trichloride in 20 ml of methylene chloride was refluxed for 3 hr. The mixture was cooled, poured over ice, basified with ammonium hydroxide 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 crystallized upon the addition of ether to give colorless prisms, mp 121°-123° C.

Workup

  1. temperaturewas refluxed for 3 hr
  2. temperatureThe mixture was cooled
  3. additionpoured over ice
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customThe residue crystallized upon the addition of ether
  9. customto give colorless prisms, mp 121°-123° C.

Sources & evidence

ORD record
ord-8a5537dfc51744e4b595d49ac5ce8647
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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