Methyl Isocyanate → N-methyl-1-butylhydrazine-carboxamide

HRID 1247871Notes

Reaction equation

HRID 1247871 reaction equation
Cl.[CH2:2]([NH:6][NH2:7])[CH2:3][CH2:4][CH3:5].[CH3:8][N:9]=[C:10]=[O:11]>O1CCCC1>[CH3:8][NH:9][C:10]([N:6]([CH2:2][CH2:3][CH2:4][CH3:5])[NH2:7])=[O:11]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 93308Butylhydrazine hydrochloride

Product 1

HCID 20279736N-methyl-1-butylhydrazine-carboxamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2.42 g n-butylhydrazine hydrochloride in 15 mL tetrahydrofuran was degassed and stirred under nitrogen with cooling (water bath) while 1.68 g of powdered potassium hydroxide was added. Stirring and cooling continued as 0.86 g (0.015 mole) methyl isocyanate in 15 mL tetrahydrofuran was added dropwise. The resulting mixture was allowed to stir at room temperature overnight. The solution was filtered and the filtrate evaporated to yield a colorless liquid. Vacuum distillation gave 82.7% N-methyl-1-butylhydrazine-carboxamide, b.p. 116°-118° C. at 0.06 torr. The compound crystallized upon standing m.p. 48°-50° C. Its structure was confirmed by NMR analysis.

Workup

  1. customwas degassed
  2. temperaturewith cooling (water bath) while 1.68 g of powdered potassium hydroxide
  3. additionwas added
  4. stirringStirring
  5. temperaturecooling
  6. additionwas added dropwise
  7. stirringto stir at room temperature overnight
  8. filtrationThe solution was filtered
  9. customthe filtrate evaporated
  10. customto yield a colorless liquid
  11. distillationVacuum distillation

Sources & evidence

ORD record
ord-60f69a8fd9ce4f6b98fd3ad3ff56d4f0
Source dataset
uspto-grants-1985_06
Patent number
US04521325

Reaction notes

Loading…