Methyl Isocyanate → 1-[3-Cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionyl]-3-methyl-urea

HRID 1860208Notes

Reaction equation

HRID 1860208 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][N:23]=[C:24]=[O:25]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:12]=2)[C:8]([NH:10][C:24]([NH:23][CH3:22])=[O:25])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 186266393-Cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionamide

Product 1

HCID 186266161-[3-Cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionyl]-3-methyl-ureaYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionamide (303 mg, 1.0 mmol) in toluene (5 mL) was treated with methyl isocyanate (0.59 mL, 10 5 mmol). The resulting solution was heated to reflux for 24 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl afforded 1-[3-cyclopentyl-2-(4-fluoro-3-trifluoromethyl-phenyl)-propionyl]-3-methyl-urea (360 mg, 49.2%) as a pale yellow oil: FAB-HRMS m/e calcd for C17H20F4N2O2 (M+H)+361.1539, found 361.1534.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 h
  3. concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-7458307f594d4b00b79085aadef0982c
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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