1-Bromopentane → 1-Benzyloxy-3-(4-butylphenyl)-1-pentylurea

HRID 976629

Reaction equation

HRID 976629 reaction equation
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O.O>[CH2:3]([O:10][N:11]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:12]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 199673681-Benzyloxy-3-(4-butylphenyl)urea

Product 1

HCID 199674451-Benzyloxy-3-(4-butylphenyl)-1-pentylureaYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.14 g of 80% in mineral oil, 4.7 mmol) was added to a solution of 1-benzyloxy-3-(4-butylphenyl)urea (1.25 g, 4.2 mmol) in N,N-dimethylformamide (5 mL). The reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature then 1-bromopentane (0.63 g, 4.2 mmol) was added. The reaction mixture was heated at 90° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water and then extracted with diethyl ether. The organic layer was washed with water, dried with magnesium sulfate and then concentrated to provide 1.47 g of crude product as a brown oil. This material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes) to provide 0.96 g of 1-benzyloxy-3-(4-butylphenyl)-1-pentylurea as an oil.

Workup

  1. temperatureThe reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere
  2. temperatureThe reaction mixture was heated at 90° C. overnight
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customto provide 1.47 g of crude product as a brown oil
  9. customThis material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-161e249b100a4b4390ab9e5b292ca3c8
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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