tert-Butyl isocyanate → N-(1-cyanoethyl)-N'-(1,1-dimethylethyl)urea

HRID 263265

Reaction equation

HRID 263265 reaction equation
[NH2:1][CH:2]([CH3:5])[C:3]#[N:4].[C:6]([N:10]=[C:11]=[O:12])([CH3:9])([CH3:8])[CH3:7]>O1CCCC1>[C:3]([CH:2]([NH:1][C:11]([NH:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH3:5])#[N:4]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 411840Propanenitrile, 2-amino-

Product 1

HCID 21316847N-(1-cyanoethyl)-N'-(1,1-dimethylethyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 21.1 g (0.3 mole) 2-aminopropionitrile in 300 ml. dry tetrahydrofuran under a nitrogen atmosphere, there is added 30.7 g (0.3 mole) t-butyl isocyanate (97%). The resulting mixture is heated at reflux for five hours. At the end of this period, the tetrahydrofuran is removed at reduced pressure. The solid is recrystallized from methanol:water, 60:40, to give N-(1-cyanoethyl)-N'-(1,1-dimethylethyl)urea, m.p. 161°-3°.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for five hours
  3. customAt the end of this period, the tetrahydrofuran is removed at reduced pressure
  4. customThe solid is recrystallized from methanol

Sources & evidence

ORD record
ord-f6408094509d48d58ea659d4a8ff15bc
Source dataset
uspto-grants-1979_05
Patent number
US04156738

Linked notes

Loading…