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

HRID 1419342Notes

Reaction equation

HRID 1419342 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): δ9.48 (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-72bfe07882064384922f690827cdc9a1
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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