Methyl Isocyanate → 1[(3,4-Dichloro-phenyl)-(tetrahydro-pyran-4-yloxy)-acetyl]-3-methyl-urea

HRID 397211Notes

Reaction equation

HRID 397211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([O:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:20][N:21]=[C:22]=[O:23]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([O:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:10]([NH:12][C:22]([NH:21][CH3:20])=[O:23])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18172601Rac-2-(3,4-dichloro-phenyl)-2-(tetrahydro-pyran-4-yloxy)-acetamide

Product 1

HCID 101331781[(3,4-Dichloro-phenyl)-(tetrahydro-pyran-4-yloxy)-acetyl]-3-methyl-ureaYield 21.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of rac-2-(3,4-dichloro-phenyl)-2-(tetrahydro-pyran-4-yloxy)-acetamide (278 mg, 0.91 mmol) in toluene (10 mL) was treated with methyl isocyanate (0.08 mL, 1.37 mmol). The resulting solution was heated at reflux for 24 h and then the cooled reaction was concentrated in vacuo. The resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20/80 hexanes/ethyl acetate) to afford [1[(3,4-dichloro-phenyl)-(tetrahydro-pyran-4-yloxy)-acetyl]-3-methyl-urea (70 mg, 21% yield) as a colorless oil: EI-HRMS m/e calcd for C15H18N2Cl2O4 (M+) 360.0643, found 360.0865.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 24 h
  3. customthe cooled reaction
  4. concentrationwas concentrated in vacuo
  5. customThe resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20/80 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-0660eb79713d420cbdbdfaab482bbd15
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

Loading…