Acetic Acid → (S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 1632169Notes

Reaction equation

HRID 1632169 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])[C@H:10]([CH3:23])[N:9]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI.C(O)(=O)C>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])[C@H:10]([CH3:23])[N:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3033985Meclonazepam

Product 1

HCID 54101851(S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

100 g (0.3 mol) of (S)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 700 ml of dry acetone. The solution is treated with 79 ml of ground potassium carbonate and with 31.4 ml of methyl iodide and the mixture is stirred at room temperature for 4 hours. The mixture is treated with 30 ml of glacial acetic acid and evaporated. The residue is treated with an ice/water mixture and extracted several times with methylene chloride. The organic phase is washed with water, dried over sodium sulphate, concentrated and treated with methanol. After filtering off the separated crystals, there is obtained (S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 159°; [α]25D =+381.2° (1 percent solution in methylene chloride).

Workup

  1. customevaporated
  2. additionThe residue is treated with an ice/water mixture
  3. extractionextracted several times with methylene chloride
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. additiontreated with methanol
  8. filtrationAfter filtering off the separated crystals

Sources & evidence

ORD record
ord-ca2b3ea5030b46fa9b4bb9ecb07b544a
Source dataset
uspto-grants-1984_10
Patent number
US04474777

Reaction notes

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