Triethylamine → N-isobutoxycarbonyl-N,N'-dimethylhydrazine

HRID 1588807Notes

Reaction equation

HRID 1588807 reaction equation
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16]>C(Cl)Cl>[CH2:18]([O:17][C:15]([N:4]([CH3:3])[NH:5][CH3:6])=[O:16])[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 62365Isobutyl chloroformate

Product 1

HCID 19753838N-isobutoxycarbonyl-N,N'-dimethylhydrazineYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N,N'-dimethylhydrazine dihydrochloride (940 mg) and triethylamine (2.15 g) in methylene chloride (30 ml) which was cooled to 0° C., was added isobutyl chloroformate (970 mg). The mixture was stirred at 0° C. for 1 hour. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml) and the solution was washed with 1M sodium bicarbonate solution and water successively, and dried over sodium sulfate. The solvent was evaporated to give N-isobutoxycarbonyl-N,N'-dimethylhydrazine (922 mg) as an oil.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washthe solution was washed with 1M sodium bicarbonate solution and water successively
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9a30a0cbc2ac49bca37521fcf05b5fe3
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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