Water → 3-Benzyl-1-(2-bromo-5-trifluoromethyl-benzyl)-1-ethyl-urea

HRID 554656Notes

Reaction equation

HRID 554656 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:3]=1[CH2:4][NH:5][CH2:6][CH3:7].C(N(CC)CC)C.[CH2:23]([N:30]=[C:31]=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C(Cl)Cl>[CH2:23]([NH:30][C:31](=[O:32])[N:5]([CH2:4][C:3]1[CH:8]=[C:9]([C:12]([F:13])([F:14])[F:15])[CH:10]=[CH:11][C:2]=1[Br:1])[CH2:6][CH3:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 66603999(2-Bromo-5-trifluoromethyl-benzyl)-ethyl-amine

Product 1

HCID 574588013-Benzyl-1-(2-bromo-5-trifluoromethyl-benzyl)-1-ethyl-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amine (2.35 g, 8.33 mmol) in CH2Cl2 (24 mL) was added triethylamine (1.8 mL, 12.5 mmol), followed by benzyl isocyanate (1.22 mL, 10.0 mmol), and the reaction was stirred at room temperature for 50 minutes. The mixture was worked up with CH2Cl2 and H2O, and the combined organic layers were dried, filtered, and concentrated. The residue was dissolved in CH2Cl2 and filtered to remove solids, and the filtrate was purified by silica gel chromatography to give 3-benzyl-1-(2-bromo-5-trifluoromethyl-benzyl)-1-ethyl-urea.

Workup

  1. customthe combined organic layers were dried
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. filtrationfiltered
  6. customto remove solids
  7. customthe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a2b1fcd13e0b4d7da9e2c55f092e963a
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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