Methyl iodide → 5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 354738Notes

Reaction equation

HRID 354738 reaction equation
[F: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:10]([CH3:24])([CH3:23])[N:9]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F: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]([CH3:25])[C:11](=[O:22])[C:10]([CH3:24])([CH3:23])[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 205061515-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

18.2 g (0.056 mol) of 5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 150 ml of dry acetone, treated with 18 g of powdered potassium carbonate and 9 ml of methyl iodide and stirred at room temperature for 21/2 hours. Subsequently, the reaction mixture is evaporated and the residue is partitioned between methylene chloride and water. After separating the organic phase, it is extracted several times more with methylene chloride. The combined organic extracts are then dried and evaporated. The residue is recrystallized from benzene/hexane/petroleum ether and gives 5-(o-fluorphenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 128°-129°.

Workup

  1. customSubsequently, the reaction mixture is evaporated
  2. customthe residue is partitioned between methylene chloride and water
  3. customAfter separating the organic phase, it
  4. extractionis extracted several times more with methylene chloride
  5. customThe combined organic extracts are then dried
  6. customevaporated
  7. customThe residue is recrystallized from benzene/hexane/petroleum ether

Sources & evidence

ORD record
ord-3def78dc81f44728989a2ea9c7f0b1f9
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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