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

HRID 1810318Notes

Reaction equation

HRID 1810318 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(C(C)C)CC)(C)C.[C:25](Cl)(Cl)=[O:26].C(N(CC)CC)C.[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[CH2:36]([NH:43][C:25](=[O:26])[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:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 6371PhosgeneHCID 7504BenzylamineHCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 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 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amine (1.5 g, 5.3 mmol) in CH2Cl2 (20 mL) at 0° C. was added diisopropylethylamine (1.7 mL, 13.3 mmol). Phosgene (1.9M in toluene; 4.2 mL, 8.0 mmol) was then added dropwise, and the reaction was stirred for 2 hours. Triethylamine (1.48 mL, 10.6 mmol) was added, followed by benzylamine (0.87 mL, 8.0 mmol), and the reaction was stirred at room temperature for 2.5 hours. After work-up with CH2Cl2 and H2O, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature for 2.5 hours
  2. customAfter work-up with CH2Cl2 and H2O, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6b9c78a785b34415ab46d49b8bee20c9
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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