Methyl iodide → HCID 70595015, compound

HRID 1733031Notes

Reaction equation

HRID 1733031 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([Cl:22])[CH:19]=[N:18]2)=[C:13]([Cl:23])[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:25]([O-])C.[Na+].CI>C(O)C>[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:25])([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([Cl:22])[CH:19]=[N:18]2)=[C:13]([Cl:23])[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 2723922Sodium ethoxideHCID 53643792HCID 53643792, compound

Product 1

HCID 70595015HCID 70595015, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

7.38 g (20 mmoles) of 3-chloro-4-(4-chloropyrazol-1-yl)phenylmalonic acid diethyl ester are dissolved in 20 ml of absolute ethanol; a solution of sodium ethanolate in ethanol (consisting of 470 mg of sodium in 20 ml of ethanol) is added; stirring is effected at 40° C. for half an hour and 2.84 g (20 mmoles) of methyl iodide are added. Boiling under reflux is effected for 4 hours; again, 2.84 g of methyl iodide are added, followed by heating for a further 2 hours, concentration, and taking up with diethyl ether. The ethereal phase is washed with sodium hydrogen sulphite solution and water, dried and concentrated. Methyl-[3-chloro-4-(4-chloropyrazol-1-yl) phenyl] malonic acid diethyl ester is obtained.

Workup

  1. waitis effected at 40° C. for half an hour
  2. temperatureBoiling under reflux
  3. temperatureby heating for a further 2 hours
  4. concentrationconcentration
  5. washThe ethereal phase is washed with sodium hydrogen sulphite solution and water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3dffcd76a96b4739a116b12d4d15809d
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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