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

HRID 612637Notes

Reaction equation

HRID 612637 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-3a67e61e17334ba8beb2be138dac7c9b
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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