Dimethylformamide → HCID 20523284, compound

HRID 223228Notes

Reaction equation

HRID 223228 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH2:16][OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.CI.[CH3:22]N(C)C=O.[H-].[Na+]>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH2:16][O:17][CH3:22])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212899527-chloro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 20523284HCID 20523284, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.22 g (8 mmol) of 7-chloro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 0.6 ml (10 mmoL) of methyl iodide and 20 ml of dry dimethylformamide is treated with 0.4 g (9 mmol) of sodium hydride (55 percent oil dispersion, washed with n-hexane) and the mixture is stirred at room temperature for 23 hours. The mixture is poured into 50 ml of water and extracted four times with methylene chloride. The methylene chloride solution is dried over magnesium sulphate and evaporated. The crude product is chromatographed on silica gel using methylene chloride containing 1% of methanol for the elution. By subsequent recrystallization from ethyl acetate/n-hexane there is obtained 7-chloro-4,5-dihydro-3-(methoxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 143°-144°.

Workup

  1. extractionextracted four times with methylene chloride
  2. dry with materialThe methylene chloride solution is dried over magnesium sulphate
  3. customevaporated
  4. customThe crude product is chromatographed on silica gel
  5. washfor the elution
  6. customBy subsequent recrystallization from ethyl acetate/n-hexane there

Sources & evidence

ORD record
ord-361118361581463ab1f9ff1c9894006f
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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