Methanol → 1-[2-(3,4-Dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionyl]-3-methyl-urea

HRID 854720Notes

Reaction equation

HRID 854720 reaction equation
CO[C:3](=[O:19])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][O:7]1.[CH3:20][NH:21][C:22]([NH2:24])=[O:23].C[O-].[Mg+2].C[O-].CO>>[Cl:18][C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][O:7]2)[C:3]([NH:24][C:22]([NH:21][CH3:20])=[O:23])=[O:19])[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 674821162-(3,4-Dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester

Product 1

HCID 98629841-[2-(3,4-Dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionyl]-3-methyl-urea

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester (617 mg, 2.04 mmol), methylurea (302 mg, 4.07 mmol), and a solution of magnesium methoxide in methanol (7.4 wt. % , 4.63 mL, 3.06 mmol) was heated at 100° C. for 8 h. After this time, the reaction mixture was concentrated in vacuo, dissolved in ethyl acetate (50 mL), and then filtered through a pad of silica gel. The organics were then concentrated in vacuo to give the crude product. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 1-[2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionyl]-3-methyl-urea as a white solid: EI-HRMS m/e calcd for C15H18Cl2N2O3 (M+) 344.0694. found 344.0699.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate (50 mL)
  3. filtrationfiltered through a pad of silica gel
  4. concentrationThe organics were then concentrated in vacuo
  5. customto give the crude product

Sources & evidence

ORD record
ord-0ab4773d46f84336849284026e453bb5
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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