Iodoethane → 8-fluoro-3-(3-ethoxy-3-methyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1607009Notes

Reaction equation

HRID 1607009 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]#[C:16][C:17]([OH:20])([CH3:19])[CH3:18])=[C:10]3[CH2:9][N:8]([CH3:21])[C:7](=[O:22])[C:6]=2[CH:23]=1.[CH2:24](I)[CH3:25].[OH-].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]#[C:16][C:17]([O:20][CH2:24][CH3:25])([CH3:19])[CH3:18])=[C:10]3[CH2:9][N:8]([CH3:21])[C:7](=[O:22])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 198515648-fluoro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198516038-fluoro-3-(3-ethoxy-3-methyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g (9.5 mmol) of 8-fluoro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one were dissolved in 20 ml of N,N-dimethylformamide and treated at 3° with 2.97 g (19 mmol) of ethyl iodide and 2.13 g of freshly powdered potassium hydroxide (38 mmol). After stirring for 5 minutes the cooling bath was removed and the mixture was left to come to room temperature. The reaction mixture was then poured into 200 ml of water, acidified with 4N hydrochloric acid and extracted four times with methylene chloride. The combined extracts were washed five times with water, dried over magnesium sulphate and evaporated. By recrystallization of the crude product from ethyl acetate and hexane there was obtained 8-fluoro-3-(3-ethoxy-3-methyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 136°-138°.

Workup

  1. customwas removed
  2. waitthe mixture was left
  3. customto come to room temperature
  4. additionThe reaction mixture was then poured into 200 ml of water
  5. extractionextracted four times with methylene chloride
  6. washThe combined extracts were washed five times with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customBy recrystallization of the crude product from ethyl acetate

Sources & evidence

ORD record
ord-fd8b409237ee4e339c188471799df53f
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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