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

HRID 397209Notes

Reaction equation

HRID 397209 reaction equation
[CH:1]1([O:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:9]([NH2:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][N:21]=[C:22]=[O:23]>C1(C)C=CC=CC=1>[CH:1]1([O:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:9]([NH:11][C:22]([NH:21][CH3:20])=[O:23])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18172605Rac-2-cyclohexyloxy-2-(3,4-dichloro-phenyl)-acetamide

Product 1

HCID 99469001-[Cyclohexyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-ureaYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of rac-2-cyclohexyloxy-2-(3,4-dichloro-phenyl)-acetamide (291 mg, 0.96 mmol) in toluene (10 mL) was treated with methyl isocyanate (0.09 mL, 1.44 mmol). The resulting solution was heated at reflux for 24 h and then the cooled reaction was concentrated in vacuo. The reaction product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) to give 1-[cyclohexyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea (301 mg, 87% yield) as a colorless oil: EI-HRMS m/e calcd for C16H20N2Cl2O3 (M+H)+ 359.0929, found 359.0922.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 24 h
  3. customthe cooled reaction
  4. concentrationwas concentrated in vacuo
  5. customThe reaction product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-16fe94b884d14a55a06fbc460e956c81
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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