Ethyl isocyanate → 1-[3-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-urea

HRID 1860141Notes

Reaction equation

HRID 1860141 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:10][C:22]([NH:21][CH2:19][CH3:20])=[O:23])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 186266403-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide

Product 1

HCID 186266331-[3-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-ureaYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide (98 mg, 0.33 mmol) in toluene (10 mL) was treated with ethyl isocyanate (0.03 mL, 0.42 mmol). The resulting solution was heated under reflux for 24 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230400 mesh, 90/10 hexanes/ethyl afforded 1-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-urea (29 mg, 26%) as a white foam: EI-HRMS m/e calcd for C17H22Cl2N2O2 (M+) 356.1058, found 356.1066.

Workup

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

Sources & evidence

ORD record
ord-a565c27a95a84030aa6c8bad22641d81
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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