Methyl iodide → HCID 59185967, compound

HRID 388270Notes

Reaction equation

HRID 388270 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])/[CH:6]=[N:7]/[NH:8][C:9](=[O:19])[CH:10]([O:17][CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.I[CH3:26].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])/[CH:6]=[N:7]/[N:8]([CH3:26])[C:9](=[O:19])[CH:10]([O:17][CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59185911HCID 59185911, compound

Product 1

HCID 59185967HCID 59185967, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-N′-(3,4-Dimethoxybenzylidene)-2-methoxy-N-methyl-2-phenylacetohydrazide (12-70) was synthesized according to the method used for the preparation of Example 6. To a solution of (E)-N′-(3,4-dimethoxybenzylidene)-2-methoxy-2-phenylacetohydrazide (12-21) (0.56 g) in anhydrous DMF in an oven-dried flask under argon was added iodomethane (1 eq) then NaH (60% in oil; 1.1 eq) was added and the mixture stirred for 2 hours. The reaction was quenched with brine and further diluted with water. The aqueous mixture was extracted with EtOAc and the combined organics were washed with water three times, brine once, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography provided the product (12-70) (0.4 g, 70%).

Workup

  1. custom(E)-N′-(3,4-Dimethoxybenzylidene)-2-methoxy-N-methyl-2-phenylacetohydrazide (12-70) was synthesized
  2. customused for the preparation of Example 6
  3. customThe reaction was quenched with brine
  4. additionfurther diluted with water
  5. extractionThe aqueous mixture was extracted with EtOAc
  6. washthe combined organics were washed with water three times, brine once
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography

Sources & evidence

ORD record
ord-acae49ace1b545f6833960d2fd4b09e6
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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