Triethylamine → HCID 67272794, compound

HRID 250908Notes

Reaction equation

HRID 250908 reaction equation
[CH2:1]([N:6]=[C:7]=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:9][C:10]1[CH:11]=[C:12](CN)[CH:13]=[CH:14][CH:15]=1.[CH2:18]([N:20](CC)CC)C>ClCCl>[Br:9][C:10]1[CH:11]=[C:12]([N:20]([CH3:18])[C:7]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:8])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 206036Pentane, 1-isocyanato-HCID 457587Benzenemethanamine, 3-bromo-

Product 1

HCID 67272794HCID 67272794, compoundYield 287.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 50.0 g (0.442 mol, 1 eq) of pentyl isocyanate in 50 mL of dichloromethane is added to a mixture of 82.2 g (0.442 mol, 1 eq) of (3-bromophenyl)methylamine in 250 mL of dichloromethane in the presence of 20 mL (0.143 mol, 0.3 eq) of triethylamine. The reaction medium is refluxed for 3 days and then hydrolyzed in 200 mL of 1N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and sodium chloride, and evaporated. 123 g of 1-(3-bromophenyl)-1-methyl-3-pentylurea are obtained. Yield=93%

Workup

  1. temperatureThe reaction medium is refluxed for 3 days
  2. extractionhydrolyzed in 200 mL of 1N hydrochloric acid solution and extracted with ethyl acetate
  3. washwashed with water and sodium chloride
  4. customevaporated

Sources & evidence

ORD record
ord-62e8a140f8a64c8d927b6b9af5bc088b
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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