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Methyl iodide → 7-chloro-4,5-dihydro-3-(3-methoxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

HRID 1606993
Notes
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Reaction equation

HRID 1606993 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]2[C:10](=[O:24])[N:11]([CH3:23])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][CH:20]([OH:22])[CH3:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:25]I>CN(C)C=O>[Cl:3][C:4]1[C:9]2[C:10](=[O:24])[N:11]([CH3:23])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][CH:20]([O:22][CH3:25])[CH3:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 198306467-chloro-4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515487-chloro-4,5-dihydro-3-(3-methoxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4.0 g (69.5 mmol) of freshly powdered potassium hydroxide was stirred for 10 minutes in 40 ml of N,N-dimethylformamide and cooled to 10°. 5.48 g (17.3 mmol) of 7-chloro-4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one and 4.94 g (35 mmol) of methyl iodide were 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 and extracted five times with methylene chloride. The combined organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After recrystallization of the residue from ethyl acetate there was obtained 7-chloro-4,5-dihydro-3-(3-methoxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one of melting point 139°-141°.

Workup

  1. temperaturecooled to 10°
  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. washThe combined organic extracts were washed four times with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customAfter recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-d7fd4b0c697b46bf993295cf6f4d5c40
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04863920

Reaction notes

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