Methyl iodide → HCID 20562349, compound

HRID 848531Notes

Reaction equation

HRID 848531 reaction equation
[CH2:1]([CH:3]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:7]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:6]=2[NH:5][C:4]1=[O:24])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([CH:3]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:7]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:6]=2[N:5]([CH3:25])[C:4]1=[O:24])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 20562348HCID 20562348, compound

Product 1

HCID 20562349HCID 20562349, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

30 g (0.092 M) of rac-3-ethyl-5-(o-fluorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 200 ml of absolute acetone, treated with 16 g of powdered potassium carbonate and 8 ml of methyl iodide and the mixture is stirred at room temperature. After 1 hour, a further 4 ml of methyl iodide are added and the mixture is stirred for a further 2.5 hours. The undissolved inorganic salts are filtered off under suction and the solution is concentrated. The residue is treated with water, the mixture is extracted with methylene chloride and the extract is dried with sodium sulphate, filtered and concentrated. After crystallisation from ethyl acetate/petroleum ether, there is obtained rac-3-ethyl-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 175°-176° C.

Workup

  1. stirringthe mixture is stirred for a further 2.5 hours
  2. filtrationThe undissolved inorganic salts are filtered off under suction
  3. concentrationthe solution is concentrated
  4. additionThe residue is treated with water
  5. extractionthe mixture is extracted with methylene chloride
  6. dry with materialthe extract is dried with sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customAfter crystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-6cb7691dc7444dc0922da92d953aba8f
Source dataset
uspto-grants-1981_10
Patent number
US04296031

Reaction notes

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