Phenyl isocyanate → N-(2-(2-Oxo-1-imidazolidinyl)ethyl)-N'-phenylurea

HRID 359465

Reaction equation

HRID 359465 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[O:9]=[C:5]1[NH:6][CH2:7][CH2:8][N:4]1[CH2:3][CH2:2][NH:1][C:17]([NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 80480N-(2-Aminoethyl)ethyleneurea

Product 1

HCID 115176N-(2-(2-Oxo-1-imidazolidinyl)ethyl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 6.5 g of commercially available 1-(2-aminoethyl)-2-imidazolidone and 50 ml benzene was added 5.5 ml of phenyl isocyanate. The strongly exothermic reaction was moderated by cooling to 25°. The mixture was stirred at 25° for 4 hr. It was cooled in ice and the mixture was filtered. The solid product was crystallized from 250 ml of acetone to give 6.8 g of white 1-[2-(2-oxo-1-imidazolidinyl)ethyl]-3-phenylurea, mp 162°-164°.

Workup

  1. customThe strongly exothermic reaction
  2. temperatureby cooling to 25°
  3. temperatureIt was cooled in ice
  4. filtrationthe mixture was filtered
  5. customThe solid product was crystallized from 250 ml of acetone

Sources & evidence

ORD record
ord-41ce921cde0a454fbb0531a060fab81b
Source dataset
uspto-grants-1991_03
Patent number
US05001141

Linked notes

Loading…