Triethylamine → N-(isopropylcarbamoyl)-N,N'-dimethylhydrazine

HRID 1649896Notes

Reaction equation

HRID 1649896 reaction equation
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(N(CC)CC)C.[CH:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15]>O1CCCC1>[CH:14]([NH:17][C:18]([N:4]([CH3:3])[NH:5][CH3:6])=[O:19])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 61277Isopropyl isocyanate

Product 1

HCID 19753751N-(isopropylcarbamoyl)-N,N'-dimethylhydrazineYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N,N'-dimethylhydrazine dihydrochloride (1.33 g) and triethylamine (2.02 g) in dry tetrahydrofuran (20 ml) which was cooled to 0° C., was added isopropyl isocyanate (851 mg). The mixture was stirred at 0° C. for 2 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml). The solution was washed with 1M sodium bicarbonate solution and water successively, and dried over magnesium sulfate. The solvent was evaporated to give N-(isopropylcarbamoyl)-N,N'-dimethylhydrazine (771 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 magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d1209649c58d499fb94657db7a6faff6
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

Loading…