Allyl isocyanate → N-(2-Cyanophenyl)-N'-prop-2-en-1-ylurea

HRID 466987Notes

Reaction equation

HRID 466987 reaction equation
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:10]([N:13]=[C:14]=[O:15])[CH:11]=[CH2:12]>>[CH2:10]([NH:13][C:14](=[O:15])[NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]#[N:9])[CH:11]=[CH2:12]

Participants

3

Reactant 2

HCID 15123Allyl isocyanateHCID 729132-Aminobenzonitrile

Product 1

HCID 14271357N-(2-Cyanophenyl)-N'-prop-2-en-1-ylureaYield 100%

Procedure

A mixture of anthranilonitrile (10.0 g, 85 mmol) and allyl isocyanate (7.5 mL, 85 mmol) was slightly heated to dissolve. The resulting solution was allowed to stir at room temperature for two days. The solid was collected by filtration and washed with ether (10 mL) to give 14.4 g (100%) of 2-(3-allylureido)benzonitrile. An analytical sample was recrystallized from ethanol. IR (KBr): 3331, 3263, 2226 (CN), 1639 cm-1. 1H NMR (300 MHz, DMSO-d6): δ3.74 (p, 2H, CH2), 5.09 (q, 1H, =CH), 5.17 (q, 1H, =CH), 5.86 (m, 1H, CH), 7.09 (t, 2H, Ar--H), 7.56 (t, 1H, Ar--H), 7.67 (d, 1H, Ar--H), 8.43 (d, 1H, Ar--H), 7.65 (d, 1H, NH), 8.54 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ41.47, 101.00, 114.97, 116.99, 120.61, 120.73, 122.22, 132.96, 133.83, 135.69, 142.66, 154.32. Anal. Calcd for C11H11N30 (201.23): C, 65.66; H, 5.51; N, 20.89. Found: C, 65.38; H, 5.51; N, 21.05.

Workup

  1. temperaturewas slightly heated to dissolve
  2. filtrationThe solid was collected by filtration
  3. washwashed with ether (10 mL)

Sources & evidence

ORD record
ord-e26542ad257c4694bc6ca3f1c121d406
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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