Allyl bromide → HCID 86606740, compound

HRID 1453816Notes

Reaction equation

HRID 1453816 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][N:6]([O:22][CH3:23])[C:7]([NH:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:5][N:6]([O:22][CH3:23])[C:7]([N:9]([CH2:3][CH:2]=[CH2:1])[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]([F:19])([F:20])[F:21])=[O:11])=[O:8]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11600272HCID 11600272, compound

Product 1

HCID 86606740HCID 86606740, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Allyl bromide (0.10 ml) was added to a suspension of 1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.25 g) and potassium carbonate (0.16 g) in N,N-dimethylformamide at 20° C., and stirred for 2 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1) to give 1-methyl-1-methoxy-3-allyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.26 g, Compound E-85).

Workup

  1. dry with materialthe organic phase dried (magnesium sulfate)
  2. customevaporated
  3. customthe residue purified by column chromatography on silica gel
  4. washeluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2478cd669c6d4e00b25b3ef75d0536f8
Source dataset
uspto-grants-2009_01
Patent number
US07476685B2

Reaction notes

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