Methanol → HCID 18626636, compound

HRID 1860155Notes

Reaction equation

HRID 1860155 reaction equation
C(O[C:4](=[O:17])[CH:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[NH2:18][C:19]([NH2:21])=[O:20].C[O-].[Mg+2].C[O-].CO>>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:4]([NH:18][C:19]([NH2:21])=[O:20])=[O:17])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1176UreaHCID 164537Methanol, magnesium salt (2:1)HCID 53673714HCID 53673714, compound

Product 1

HCID 18626636HCID 18626636, compoundYield 5.3%

Procedure

A mixture of 2-(4-chloro-phenyl)-4-methyl-pentanoic acid ethyl ester (508 mg, 1.99 mmol) and urea (239 mg, 3.99 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 4.28 mL, 2.99 mmol) was heated to reflux for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded [2-(4-chloro-phenyl)-4-methyl-pentanoyl]-urea (28.1 mg, 5.2%) as a white solid: mp 164-165° C.; EI-HRMS m/e calcd for C13H17ClN2O2 (M+) 268.0979, found 268.0972.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-ef4dd061d0564334857e8718248eeabe
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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