(S)-(-)-1-Phenylethyl isocyanate → (S)-N-(2-hydroxy-4-nitrophenyl)-N'-(methyl benzyl)urea

HRID 650093Notes

Reaction equation

HRID 650093 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][C@H:13]([N:20]=[C:21]=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[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@@H:13]([CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22]

Participants

3

Reactant 2

HCID 2724173(S)-(-)-1-Phenylethyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 54257898(S)-N-(2-hydroxy-4-nitrophenyl)-N'-(methyl benzyl)ureaYield 76.7%

Procedure

(S)-N-(2-Hydroxy-4-nitrophenyl)-N′-(methylbenzyl)urea was prepared from 2-hydroxy 4-nitro aniline (308 mg, 2.0 mmol) and (S)-methyl benzyl isocyanate (2 mmol) according to the procedure in General Method A. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (462 mg, 76%). EI-MS m/z 300(M−H)−

Workup

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

Sources & evidence

ORD record
ord-e32df085c64f4fd0ad5a97cc515a9f74
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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