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

HRID 323017Notes

Reaction equation

HRID 323017 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-853a97eb86f94e54ad2637ac61311f3e
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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