Diethyl Ether → 1-Hydroxy-1-(1-methylethyl)-3-(2,4,5-trimethylphenyl)urea

HRID 976636Notes

Reaction equation

HRID 976636 reaction equation
Cl.[CH:2]([NH:5][OH:6])([CH3:4])[CH3:3].C(OCC)C.[OH-].[Na+].[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([CH3:22])=[CH:17][C:16]=1[N:23]=[C:24]=[O:25]>O>[OH:6][N:5]([CH:2]([CH3:4])[CH3:3])[C:24]([NH:23][C:16]1[CH:17]=[C:18]([CH3:22])[C:19]([CH3:21])=[CH:20][C:15]=1[CH3:14])=[O:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 127935172,4,5-Trimethylphenyl isocyanate

Product 1

HCID 199673751-Hydroxy-1-(1-methylethyl)-3-(2,4,5-trimethylphenyl)ureaYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of N-isopropylhydroxylamine hydrochloride (1.85 g, 16.5 mmol) in water (5 mL) was combined with diethyl ether (50 mL) then cooled in an ice bath. A solution of sodium hydroxide (0.72 g, 18 mmol) in water (10 mL) was added over a 10 minute period. The reaction mixture was stirred for 10 minutes then 2,4,5-trimethylphenyl isocyanate (2.42 g, 15 mmol) was added as a solid. The reaction mixture was stirred at ambient temperature for 18 hours. A white solid was isolated by filtration then recrystallized from hexanes/ethyl acetate to provide 2.4 g of the desired product as a white crystalline solid, m.p. 176.2°-176.8° C. Analysis: Calculated for C13H20N2O2 : %C, 66.07; %H, 8.53; %N, 11.85; Found: %C, 65.85; %H, 8.35; %N, 11.68.

Workup

  1. temperaturethen cooled in an ice bath
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. customA white solid was isolated by filtration
  4. customthen recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-f41654a6867848c88c9d135abf7b1948
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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