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

HRID 464511Notes

Reaction equation

HRID 464511 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[Cl:9][C:10]1[CH:32]=[CH:31][C:13]2[C:14](=O)[C:15](=[CH:26]N(C)C)[CH2:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:12]=2[CH:11]=1>CO.C(Cl)Cl.O.CS(O)(=O)=O>[Cl:9][C:10]1[CH:32]=[CH:31][C:13]2[C:14]3[N:5]=[C:2]([CH3:3])[N:4]=[CH:26][C:15]=3[CH2:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:12]=2[CH:11]=1

Participants

8

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

Product 1

HCID 132255009-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepine

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

In five equal portions 5.5 g (58 mmole) of acetamidine hydrochloride and 15 ml (62 mmole) of a 4.12M methanol solution of sodium methoxide was added over 3 hr. to solution of 3.5 g (10 mmole) of 8-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one in 140 ml of methanol and 140 ml of methylene chloride. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water dried with anhydrous sodium sulfate, and concentrated at reduced pressure to give an amber oil. The amber oil was dissolved in 10 ml (10 mmole) of a 1M methanol solution of methanesulfonic acid and the resulting salt was precipitated by the addition of ether to give yellow prisms, mp 193°-197° C. Recrystallization from a mixture of methanol and ether gave yellow prisms, mp 197°-198° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride solution was washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto give an amber oil
  6. customthe resulting salt was precipitated by the addition of ether
  7. customto give yellow prisms, mp 193°-197° C
  8. customRecrystallization
  9. additionfrom a mixture of methanol and ether
  10. customgave yellow prisms, mp 197°-198° C.

Sources & evidence

ORD record
ord-c435df0d71e9400283a658adc145efc6
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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