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

HRID 464167Notes

Reaction equation

HRID 464167 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 4.12M 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 product 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)

Sources & evidence

ORD record
ord-9e0ee166290349e187055d44e6099a0c
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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