Methyl iodide → 4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1607014Notes

Reaction equation

HRID 1607014 reaction equation
[OH-].[K+].[OH:3][CH2:4][C:5]#[C:6][C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[N:13]([CH3:22])[CH2:12][C:11]=12.[CH3:23]I>CN(C)C=O>[CH3:23][O:3][CH2:4][C:5]#[C:6][C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[N:13]([CH3:22])[CH2:12][C:11]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 198515454,5-dihydro-3-(3-hydroxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515634,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.05 g (90 mmol) of freshly powdered potassium hydroxide was suspended in 50 ml of N,N-dimethylformamide and cooled to 3°. 6.0 g (22.5 mmol) of 4,5-dihydro-3-(3-hydroxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one and 6.39 g (45 mmol) of methyl iodide was added thereto in succession, the ice-bath was removed and the mixture was stirred for a further 1 hour. The reaction mixture was poured into 200 ml of water, acidified to pH 7 with 4N hydrochloric acid and extracted five times with methylene chloride. The combined organic extracts were dried over magnesium sulphate, evaporated and after crystallization of the residue from ethyl acetate there was obtained 4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 114°-115°.

Workup

  1. temperaturecooled to 3°
  2. customin succession, the ice-bath was removed
  3. additionThe reaction mixture was poured into 200 ml of water
  4. extractionextracted five times with methylene chloride
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. customevaporated
  7. customafter crystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-56a0e8836753487a82e6752d88f4789f
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

Loading…