Methanol → 9-chloro-7-(2-chlorophenyl)-2-isopropyl-5H-pyrimido[5,4-d][2]benzazepine

HRID 464513Notes

Reaction equation

HRID 464513 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=O)[C:11](=[CH:20]N(C)C)[CH2:10][N:9]=1.[ClH:24].[C:25]([NH2:30])(=[NH:29])[CH:26]([CH3:28])[CH3:27].CO.C[O-].[Na+]>O>[Cl:24][C:16]1[CH:17]=[CH:18][C:13]2[C:12]3[N:30]=[C:25]([CH:26]([CH3:28])[CH3:27])[N:29]=[CH:20][C:11]=3[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 27820532-Methylpropanimidamide hydrochlorideHCID 10942334Sodium MethoxideHCID 538264411-(2-Chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one

Product 1

HCID 132255069-chloro-7-(2-chlorophenyl)-2-isopropyl-5H-pyrimido[5,4-d][2]benzazepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customto give a yellow oil
  5. customCrystallization of the oil with ether
  6. customgave a light yellow solid, mp 127°-129° C
  7. customRecrystallization
  8. additionfrom a mixture of ether and petroleum ether
  9. customgave colorless rods, mp 127°-129° C.

Sources & evidence

ORD record
ord-9dc702a931804c779f9271fb1fd520cb
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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