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

HRID 976614Notes

Reaction equation

HRID 976614 reaction equation
Cl.[CH:2]([NH:5][OH:6])([CH3:4])[CH3:3].C(OCC)C.[OH-].[Na+].[CH3:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>O.C(OCC)(=O)C>[OH:6][N:5]([CH:2]([CH3:4])[CH3:3])[C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([S:15][CH3:14])=[CH:17][CH:18]=1)=[O:24]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 27333164-(Methylthio)phenyl isocyanate

Product 1

HCID 115722631-Hydroxy-1-(1-methylethyl)-3-[4-(methylthio)phenyl]ureaYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-Isopropylhydroxylamine hydrochloride (1.35 g, 12.1 mnmol) was dissolved in water (2 mL) then combined with diethyl ether (25 mL) followed by the addition of a solution of sodium hydroxide (0.48 g, 12.1 mmol) in water (2 mL). The reaction mixture was allowed to stir for several minutes then 4-(methylthio)phenyl isocyanate (2.0 g, 12.1 mmol) was added via pipette. A white precipitate formed. The reaction mixture was allowed to stir at ambient temperature overnight. The solid was isolated by filtration then dissolved in hot ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate then concentrated under vacuum. The precipitate was collected and dried to afford 1.60 g of the desired product as a crystalline solid, m.p. 150.0°-150.3° C. Analysis: Calculated for C11H16N2O2S: %C, 54.98; %H, 6.71; %N, 11.66; Found: %C, 54.96; %H, 6.53; %N, 11.61.

Workup

  1. customA white precipitate formed
  2. stirringto stir at ambient temperature overnight
  3. customThe solid was isolated by filtration
  4. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  5. concentrationthen concentrated under vacuum
  6. customThe precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-70e7638d87bf490a91f3a908d75f0fc5
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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