Methyl Isocyanate → 1-[Cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea

HRID 397206Notes

Reaction equation

HRID 397206 reaction equation
[CH:1]1([O: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.[CH3:19][N:20]=[C:21]=[O:22]>C1(C)C=CC=CC=1>[CH:1]1([O: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:21]([NH:20][CH3:19])=[O:22])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18172596Rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-acetamide

Product 1

HCID 99281201-[Cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-ureaYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-acetamide (116 mg, 0.40 mmol) in toluene (5 mL) was treated with methyl isocyanate (0.04 mL, 0.60 mmol). The resulting solution was heated to reflux for 24 h, then was cooled and was evaporated under reduced pressure. The resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) to furnish 1-[cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea (30 mg, 41% yield) as a colorless oil: EI-HRMS m/e calcd for C15H18N2Cl2O3 (M+) 288.0558, found 288.0572.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 h
  3. temperaturewas cooled
  4. customwas evaporated under reduced pressure
  5. customThe resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5d38fa0190b54316a74b77d3c0987dd4
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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