Phenyl isocyanate → N-Phenyl-N'-prop-2-yn-1-ylurea

HRID 1531840Notes

Reaction equation

HRID 1531840 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[C:5]1([N:11]=[C:12]=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[C:5]1([NH:11][C:12]([NH:4][CH2:1][C:2]#[CH:3])=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 239041Propargylamine

Product 1

HCID 14344959N-Phenyl-N'-prop-2-yn-1-ylureaYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

25 g (0.45 mol) of propargylamine dissolved in 80 ml of toluene are added dropwise to a suspension of 50 ml (0.45 mol) of phenyl isocyanate in 160 ml of toluene. The mixture is stirred for 1 h 30 min, the precipitate is filtered, washed with a small amount of toluene and then dried in a vacuum oven at 40° C. 70.7 g of product are obtained. (m.p.=133° C.).

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed with a small amount of toluene
  3. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-689a3d01e26c454d94d95384d54cd32f
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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