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

HRID 1979579Notes

Reaction equation

HRID 1979579 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6](=O)[C:7](=[CH:19]N(C)C)[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.Cl.[C:27]([NH2:30])(=[NH:29])[CH3:28].C[O-].[Na+]>CO.C(Cl)Cl.O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[N:30]=[C:27]([CH3:28])[N:29]=[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

7

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 731657308-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one 2-oxide

Product 1

HCID 132255119-Chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]-benzazepine-6-oxide

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 g (2.8 mmole) of 8-chloro-1-(2-chlorophenyl)-4-[(dimethylamino)methylene]-3,4-dihydro-5H-2-benzazepine-5-one-2-oxide, 1.0 g (11 mmole) of acetamidine hydrochloride and 2.0 ml (9.9 mmole) of a 4.46M methanol sulution of sodium methoxide in a mixture of 20 ml of methanol and 20 ml of methylene chloride was stirred at room temperature for 2 hr. The mixture 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 dryness. Recrystallization of the residue from a mixture of ether and methylene chloride gave a colorless solid, mp 215°-216° 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 to dryness
  5. customRecrystallization of the residue
  6. additionfrom a mixture of ether and methylene chloride
  7. customgave a colorless solid, mp 215°-216° C.

Sources & evidence

ORD record
ord-1ff196deb72b4eeab47450e1574d0984
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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