Triethylamine → 1-(3-Bromophenyl)-1-methyl-3-pentylurea

HRID 390637Notes

Reaction equation

HRID 390637 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 672727941-(3-Bromophenyl)-1-methyl-3-pentylureaYield 293.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 50 g (0.45 mol) of pentyl isocyanate in 50 mL of dichloromethane is added to a mixture of 82 g (0.45 mol) of (3-bromophenyl)methylamine in 250 mL of dichloromethane in the presence of 20 mL (0.14 mol) of triethylamine. The reaction medium is heated at reflux for 3 days and then hydrolyzed in 200 mL of 1 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water, with saturated sodium chloride solution and evaporated. 123 g (93%) of 1-(3-bromophenyl)-1-methyl-3-pentylurea are obtained.

Workup

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

Sources & evidence

ORD record
ord-e2f306c11a5d4963b0faa4ab64743a40
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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