Phenyl isocyanate → 1-(2-Hydroxy-5-nitro-phenyl)-3-phenyl-urea

HRID 1385331Notes

Reaction equation

HRID 1385331 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([CH:10]=1)[NH2:9])([O-:3])=[O:2].[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([NH:9][C:19]([NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:20])[CH:10]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 118181391-(2-Hydroxy-5-nitro-phenyl)-3-phenyl-ureaYield 30%

Procedure

The N-[5-nitro-2-hydroxyphenyl]-N′-phenyl urea was prepared from the 5-nitro 2-hydroxy aniline and phenyl isocyanate according to the procedure in General Method A. The product was purified by precipitation from toluene and filtering to afford the titled compound (100 mg, 30%). 1H NMR (CD3OD): d 9.48 (s, 1H, NH), 9.07 (d, J=1.56 Hz, NH), 8.55 (s, 1H), 7.80 (dd, 1H, J=6.25 Hz and J=1.56 Hz), 7.50 (d, 2H, J=6.25 Hz), 7.30 (t, 2H, J=6.25 Hz), 7.01 (m, 2H). EI-MS m/z 273 (M+H)+.

Workup

  1. customThe product was purified by precipitation from toluene
  2. filtrationfiltering

Sources & evidence

ORD record
ord-bda04c4be8944f76af48ed62fe67d29d
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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