Benzene, 1-isocyanato-2-methoxy- → CXCR2 antagonist 8

HRID 1419358Notes

Reaction equation

HRID 1419358 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]=[C:21]=[O:22]>>[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH3:12])=[O:22]

Participants

3

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 9796445CXCR2 antagonist 8Yield 27%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyphenyl)urea was prepared from 2-hydroxy 4-nitro aniline (154 mg, 1.0 mmol) and 2-methoxy phenyl isocyanate(1 mmol.) according to the procedure in General Method B. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (82 mg, 27%). EI-MS m/z 302(M-H)-

Workup

  1. customThe product was purified by dilution with methylene chloride and precipitation with hexanes
  2. filtrationFiltering

Sources & evidence

ORD record
ord-d83563300d9d4a13be29f77e5136923d
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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