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

HRID 847546Notes

Reaction equation

HRID 847546 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 1 M 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 1 M sodium bicarbonate solution and water successively
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-da1c182b910447ba86e15a53fba56fe2
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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