Methyl iodide → HCID 54178097, compound

HRID 2287896Notes

Reaction equation

HRID 2287896 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]I.[H-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH3:17])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 689895HCID 689895, compound

Product 1

HCID 54178097HCID 54178097, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N'-benzylidenehydrazinecarboxylic acid tert-butylester (2.0 g, 9.07 mmol) in anhydrous tetrahydrofuran (20 ml) was added methyl iodide (4.54 ml, 72.6 mmol) and the solution was cooled to 0° C. Sodium hydride (60% dispersion in mineral oil, 1.09 g, 27.2 mmol) was slowly added and the mixture was stirred at room temperature for 3 days. The tetrahydrofuran (50 ml) was added and the mixture was filtered. The filtrate was concentrated in vacuo and chromatographed on silica (100 g) with heptan:ethyl acetate (1:1) to give 1.97 g (93%) of N'-benzylidene-N-methylhydrazinecarboxylic acid tert-butyl ester as a yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customchromatographed on silica (100 g) with heptan:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-18f6bf26934a4f7f98741609d48ab255
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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