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

HRID 1606983Notes

Reaction equation

HRID 1606983 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]2[C:10](=[O:25])[N:11]([CH3:24])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:26]I.O>CS(C)=O>[Cl:3][C:4]1[C:9]2[C:10](=[O:25])[N:11]([CH3:24])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][C:20]([O:23][CH3:26])([CH3:22])[CH3:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 198306547-chloro-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 198515737-chloro-4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.20 g (18.6 mmol) of freshly powdered potassium hydroxide was stirred at room temperature for 5 minutes in 15 ml of dimethyl sulfoxide. 1.65 g (5 mmol) of 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one and 1.42 g (10 mmol) of methyl iodide were then added thereto in succession, whereby the temperature rises to 35°. The reaction mixture was stirred for 45 minutes and then poured into 50 ml of water. The mixture was extracted five times with methylene chloride, the combined organic phases were dried over magnesium sulphate and evaporated. After crystallization from diisopropyl ether there was obtained 7-chloro-4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 172°-174°.

Workup

  1. customrises to 35°
  2. extractionThe mixture was extracted five times with methylene chloride
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. customevaporated
  5. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-5fdb6d384f774de7baa0452452140371
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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