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

HRID 1979561Notes

Reaction equation

HRID 1979561 reaction equation
[C:1](O)(=O)C.[CH:5]([NH2:7])=[NH:6].C[O-].[Na+].[Cl:11][C:12]1[CH:34]=[CH:33][C:15]2[C:16](=O)[CH2:17][C:18](=CN(C)C)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23]C=3Cl)[C:14]=2[CH:13]=1.[CH2:35]([Cl:37])Cl>CO.O>[Cl:11][C:12]1[CH:34]=[CH:33][C:15]2[C:16]3[N:7]=[CH:5][N:6]=[CH:1][C:17]=3[CH2:18][N:19]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:35]=3[Cl:37])[C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 572766058-chloro-1-(2-chlorophenyl)-3,4-dihydro-[(dimethylamino)methylene]-5H-2-benzazepin-5-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

In five equal portions 21 g (200 mmole) of formamidine acetate and 32.5 ml (135 mmole) of a 4.12 M methanol solution of sodium methoxide was added over 3 hr to a solution of 7.2 g (20 mmole) of 8-chloro-1-(2-chlorophenyl)-3,4-dihydro-[(dimethylamino)methylene]-5H-2-benzazepin-5-one in 270 ml of methanol and 270 ml of methylene chloride. The solution was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give an amber oil. Purification by column chromatography (100 g silica gel; eluent 1:1 methylene chloride and ethyl acetate) gave end poduct mp 122°-124° C. Recrystallization from ether gave pale yellow prisms, mp 122°-125° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto give an amber oil
  6. customPurification by column chromatography (100 g silica gel; eluent 1:1 methylene chloride and ethyl acetate)
  7. customgave end
  8. customRecrystallization from ether
  9. customgave pale yellow prisms, mp 122°-125° C.

Sources & evidence

ORD record
ord-eee88f0c22424b93977396a81d77d223
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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