3-Bromopentane → 1-Benzyloxy-1-(1-ethylpropyl)-3-phenylurea

HRID 976624

Reaction equation

HRID 976624 reaction equation
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].Br[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26]>CN(C)C=O>[CH2:3]([O:10][N:11]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 2542991-(Benzyloxy)-3-phenylureaHCID 178418361HCID 178418361, compound

Product 1

HCID 199674391-Benzyloxy-1-(1-ethylpropyl)-3-phenylureaYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, a flask was charged with sodium hydride (1.15 g 60% NaH in mineral oil, 29 mmol). Residual oil was washed from the sodium hydride using several portions of hexanes. N,N-Dimethylformamide (50 mL) was added followed by the dropwise addition of a solution of 1-benzyloxy-3-phenylurea (7.0 g, 29 mmol) in N,N-dimethylformamide (20 mL). Hydrogen evolution occurred immediately. The reaction was stirred for 0.5 hr then 3-bromopentane (4.0 mL, 32 mmol) was added dropwise. The reaction mixture was heated at 60° C. for 15 hours then allowed to cool to room temperature. The reaction was quenched with water then extracted with several portions of diethyl ether. The ether extracts were combined, washed with water and brine, dried over magnesium sulfate and then concentrated to provide 8.7 g of crude product as a pale yellow solid. The crude product was purified by flash chromatography (silica gel; 9:1 hexanes:ethyl acetate)to provide 5.7 g of 1-benzyloxy-1-(1-ethylpropyl)-3-phenylurea as a white solid, m.p. 45.0°-45.6° C.

Workup

  1. washResidual oil was washed from the sodium hydride using several portions of hexanes
  2. additionN,N-Dimethylformamide (50 mL) was added
  3. temperatureto cool to room temperature
  4. customThe reaction was quenched with water
  5. extractionthen extracted with several portions of diethyl ether
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto provide 8.7 g of crude product as a pale yellow solid
  10. customThe crude product was purified by flash chromatography (silica gel; 9:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-e668a9c0b1f745288d1c305bc250af24
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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