Methyl iodide → (+)-5-(o-chlorophenyl)--1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 2199038Notes

Reaction equation

HRID 2199038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:22])[CH:10]([CH3:23])[N:9]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:24])[C:11](=[O:22])[CH:10]([CH3:23])[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 933645-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-2h-1,4-benzodiazepin-2-one

Product 1

HCID 20443626(+)-5-(o-chlorophenyl)--1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

105.7 g (0.32 mol) of crude rac-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one, dissolved in 1 liter of acetone, are treated with 88.6 g (0.64 mol) of potassium carbonate and 39.9 ml (0.64 mol) of methyl iodide and the mixture is stirred at room temperature for 22 hours. The mixture is evaporated to dryness and the residue is taken up in methylene chloride. The organic phase is washed with water, dried and evaporated. Recrystallisation of the residue from methylene chloride/ethanol gives rac-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 170°-174° C.

Workup

  1. customThe mixture is evaporated to dryness
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated
  5. customRecrystallisation of the residue from methylene chloride/ethanol

Sources & evidence

ORD record
ord-67a7f8663d6b43b297869cc6f07adc3e
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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