Water → HCID 178456605, compound

HRID 466988Notes

Reaction equation

HRID 466988 reaction equation
[CH2:1]([NH:4][C:5](=[O:15])[NH:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])[CH:2]=[CH2:3].O>C(O)C.O.N>[NH:10]=[C:9]1[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:6][C:5](=[O:15])[N:4]1[CH2:1][CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 962WaterHCID 14271357N-(2-Cyanophenyl)-N'-prop-2-en-1-ylurea

Product 1

HCID 178456605HCID 178456605, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 12896473Azane;hydrateSolvent

Procedure

A mixture of 2-(3-allylureido)benzonitrile (10.0 g, 50 mmol) in ethanol (70 mL) and 28% of ammonia water (50 mL) was heated on a steam bath with occasional stirring for 15 minutes. The mixture was then cooled to room temperature and to the mixture was added water (100 mL). The solid was collected by filtration and was recrystallized from methanol with a few drops of ammonia water to give 8.4 g (84%) of 3,4-dihydro-4-imino-3-allyl-2(1H)-quinazolinone, mp 223°-224° C. IR (KBr): 3284, 3203, 3147, 1691, 1582 cm-1. 1H NMR (300 MHz, DMSO-d6): δ4.61 (d, 2H, =CH2), 5.08 (q, 2H, CH2), 5.85 (m, 1H, =CH), 7.07 (m, 2H, Ar--H), 7.46 (t, 1H, Ar--H), 8.04 (d, 1H, Ar--H), 8.85 (br s, 1H, NH), 10.74 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ42.54, 115.08, 115.81, 122.09, 126.13, 132.77, 133.15, 137.01, 149.76. Anal. Calcd for C11H11N3O; C, 65.63; H, 5.56; N, 20.87. Found: C, 65.67; H, 5.51; N, 20.86.

Workup

  1. temperaturewas heated on a steam bath
  2. filtrationThe solid was collected by filtration
  3. customwas recrystallized from methanol with a few drops of ammonia water

Sources & evidence

ORD record
ord-84b9e884a2654fd5a742a3899bd854e8
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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