Water → HCID 20301784, compound

HRID 1732819Notes

Reaction equation

HRID 1732819 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.CI.[C:23](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:23])[CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[N:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:6]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20301725HCID 20301725, compound

Product 1

HCID 20301784HCID 20301784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28.6 g of 8-chloro-4-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one in 100 ml dimethylformamide is stirred with 18 g methyl iodide and 14 g anhydrous potassium carbonate for 2 hours on a boiling water bath. The reaction mixture is poured into 500 ml water and extracted with ether several times. The ethereal extracts are washed with water and dried over sodium sulfate. Upon distilling off the solvent, the crystalline residue is recrystallized from acetic acid ethyl ester. The yield is 24.5 g having an m.p.=113° C.-114° C. (82% of the theory).

Workup

  1. extractionextracted with ether several times
  2. washThe ethereal extracts are washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationUpon distilling off the solvent
  5. customthe crystalline residue is recrystallized from acetic acid ethyl ester

Sources & evidence

ORD record
ord-60f8b8d4815f4d57a0008033911bd02c
Source dataset
uspto-grants-1980_12
Patent number
US04239684

Reaction notes

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