Diethyl Ether → 1-Hydroxy-1-methyl-3-[4-(methylthio)phenyl]urea

HRID 976613Notes

Reaction equation

HRID 976613 reaction equation
Cl.[CH3:2][NH:3][OH:4].C(OCC)C.[OH-].[Na+].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>O>[OH:4][N:3]([CH3:2])[C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=1)=[O:22]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 77906N-methylhydroxylamine hydrochlorideHCID 27333164-(Methylthio)phenyl isocyanate

Product 1

HCID 115937101-Hydroxy-1-methyl-3-[4-(methylthio)phenyl]ureaYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-Methylhydroxylamine hydrochloride (1.1 g, 13 mmol) was dissolved in water (2 mL) then combined with diethyl ether (15 mL). The mixture was cooled in an ice bath then combined with a solution of sodium hydroxide (0.53 g, 13 mmol) in water (2 mL). The reaction mixture was allowed to stir for several minutes then 4-(methylthio)phenyl isocyanate (2.1 g, 13 mmol) was added dropwise via Pasteur pipette. A heavy white precipitate formed almost immediately. Diethyl ether (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature overnight. The solid was isolated by filtration then recrystallized from 1,2-dichloroethane to afford 1.65 g of the desired product as a white crystalline solid, m.p. 146°-148° C. Analysis: Calculated for C9H12N2O2S: %C, 50.93; %H, 5.70; %N, 13.20; Found: %C, 50.82; %H, 5.63; %N, 13.11.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customA heavy white precipitate formed almost immediately
  3. stirringto stir at ambient temperature overnight
  4. customThe solid was isolated by filtration
  5. customthen recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-8c58796269fc4d0491495667a9bf2ea3
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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