Diethyl Ether → 1-Benzyloxy-3-(4-butylphenyl)urea

HRID 976628Notes

Reaction equation

HRID 976628 reaction equation
C(OCC)C.Cl.[CH2:7]([O:14][NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[CH2:18]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)[CH2:19][CH2:20][CH3:21]>O>[CH2:7]([O:14][NH:15][C:29]([NH:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:18][CH2:19][CH2:20][CH3:21])=[CH:23][CH:24]=1)=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 102312Benzyloxyamine hydrochlorideHCID 27963134-Butylphenyl isocyanate

Product 1

HCID 199673681-Benzyloxy-3-(4-butylphenyl)ureaYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Diethyl ether (10 mL) was added to a suspension of O-benzylhydroxylamine hydrochloride (0.82 g, 5.1 mmol) in water (1 mL). A solution of sodium hydroxide (0.23 g, 5.8 mmol) in water (1 mL) was added and the mixture was stirred for several minutes. The aqueous layer was removed by pipette and extracted with diethyl ether (3 mL). The ether extract was added to the reaction flask. 4-Butylphenyl isocyanate (0.90 g, 5.1 mole) was added to the reaction flask via pipette in a single portion. A mild reflux occurred. The reaction mixture was allowed to stir at ambient temperature for 15 minutes then purified by flash chromatography (silica gel; 1:4 ethyl acetate:hexanes) to provide 1.25 g of 1-benzyloxy-3-(4-butylphenyl)urea as a fluffy white solid, m.p. 90.6°-91.4° C.

Workup

  1. customThe aqueous layer was removed by pipette
  2. extractionextracted with diethyl ether (3 mL)
  3. extractionThe ether extract
  4. additionwas added to the reaction flask
  5. temperatureA mild reflux
  6. stirringto stir at ambient temperature for 15 minutes
  7. customthen purified by flash chromatography (silica gel; 1:4 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-200dd5cd30574eb1bc6e00ccdce855fb
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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