Sodium Hydroxide → 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606972Notes

Reaction equation

HRID 1606972 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:23])[CH2:10][C:11]3[N:12]([C:13](=O)[NH:14][C:15]=3[C:16]#[C:17]C(O)(C)C)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:24].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 703945457-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-one

Product 1

HCID 198515337-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

660 mg (2 mmol) of 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-one was heated to boiling under reflux overnight with 80 mg of sodium hydroxide in 10 ml of toluene. After evaporation of the solvent the residue was dissolved in methylene chloride and the solution was washed twice with water, dried over magnesium sulphate and evaporated. After recrystallization of the residue from ethyl acetate there was obtained 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 200°-201°.

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customAfter recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-b7cc5f1888334266a16039bfa0431e1d
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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