Dimethylformamide → HCID 20523288, compound

HRID 223226Notes

Reaction equation

HRID 223226 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]([CH3:18])[CH2:8][C:7]=12.CI.[CH3:21]N(C)C=O.[H-].[Na+]>O>[CH3:21][O:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]([CH3:18])[CH2:8][C:7]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 198516024,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 20523288HCID 20523288, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.1 g (4.5 mmol) of 4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 0.3 ml (5.0 mmol) of methyl iodide and 10 ml of dry dimethylformamide is treated with 0.2 g (4.5 mmol) of sodium hydride (55 percent oil dispersion, washed with n-hexane) and the mixture is stirred at room temperature for about 16 hours. The mixture is poured into 70 ml of water and extracted three times with chloroform. The chloroform solution is washed once with water, dried over magnesium sulphate and evaporated. The crude product is chromatographed on silica gel while eluting with chloroform containing 5% of methanol. Recrystallization of the material obtained from ethyl acetate/hexane yields 4,5-dihydro-3-(methoxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 115°-116°.

Workup

  1. extractionextracted three times with chloroform
  2. washThe chloroform solution is washed once with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is chromatographed on silica gel
  6. washwhile eluting with chloroform containing 5% of methanol
  7. customRecrystallization of the material
  8. customobtained from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a7146e9a877432793c54eb943e4591e
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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