Water → HCID 86626096, compound

HRID 390645Notes

Reaction equation

HRID 390645 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:10][C:11]1[CH:16]=[C:15](/[CH:17]=[C:18](\[O:23][CH3:24])/[C:19]([O:21][CH3:22])=[O:20])[CH:14]=[CH:13][C:12]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]([CH3:44])[C:32]([O:34]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH:26]=1)[CH2:7][CH2:8][CH3:9].O.C(OCC)(=O)C>CN(C)C=O>[CH2:6]([O:10][C:11]1[CH:16]=[C:15](/[CH:17]=[C:18](\[O:23][CH3:24])/[C:19]([O:21][CH3:22])=[O:20])[CH:14]=[CH:13][C:12]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]([CH3:44])[C:32]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:34])[CH:26]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 8857Ethyl AcetateHCID 86626097HCID 86626097, compound

Product 1

HCID 86626096HCID 86626096, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.075 mL (0.75 mmol) of n-butylamine is added to a solution of 0.4 g (0.6 mmol) of methyl (Z)-3-{2-butoxy-3′-[methyl-(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}-2-methoxyacrylate in 5 mL of dimethylformamide. The reaction mixture is rapidly placed in an oil bath preheated to 80° C. and then stirred at 80° C. for 3 hours. After cooling, the reaction is stopped by addition of 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture to give 0.2 g (67%) of methyl (Z)-3-[2-butoxy-3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylate in the form of a colorless oil.

Workup

  1. customThe reaction mixture is rapidly placed in an oil bath
  2. custompreheated to 80° C.
  3. temperatureAfter cooling
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents are evaporated off
  7. customThe crude product obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-1849174baab3457aa618cac34620b518
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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