Water → N,1-dibutylhydrazinecarboxamide

HRID 1247872Notes

Reaction equation

HRID 1247872 reaction equation
O.Cl.[CH2:3]([NH:7][NH2:8])[CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:11]([N:15]=[C:16]=[O:17])[CH2:12][CH2:13][CH3:14]>O1CCCC1>[CH2:11]([NH:15][C:16]([N:7]([CH2:3][CH2:4][CH2:5][CH3:6])[NH2:8])=[O:17])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8110Butyl isocyanateHCID 14797Potassium HydroxideHCID 93308Butylhydrazine hydrochloride

Product 1

HCID 19905055N,1-dibutylhydrazinecarboxamideYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (water bath), stirred mixture of 2.42 g n-butylhydrazine hydrochloride in 15 mL tetrahydrofuran was added 1.7 g powdered potassium hydroxide. The resulting mixture was stirred and maintained under a nitrogen atmosphere as n-butyl isocyanate (1.49 g, 0.015 moles) in 30 mL tetrahydrofuran was added dropwise. After addition, the solution was stirred overnight at ambient temperature. Work up as in Example 5 above yielded 1.5 g N,1-dibutylhydrazinecarboxamide b.p. 135°-6° C. at 0.08 torr, m.p. 34°-36° C. This structure was confirmed by NMR analysis.

Workup

  1. additionwas added 1.7 g
  2. stirringThe resulting mixture was stirred
  3. additionwas added dropwise
  4. additionAfter addition
  5. stirringthe solution was stirred overnight at ambient temperature

Sources & evidence

ORD record
ord-012f2365cc964bd4abf05aa31c506d23
Source dataset
uspto-grants-1985_06
Patent number
US04521325

Reaction notes

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