Water → ethyl (Z)-3-[3'-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate

HRID 390683Notes

Reaction equation

HRID 390683 reaction equation
[CH2:1]([O:3]/[C:4](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:36])[C:24]([O:26]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH2:37]([NH2:41])[CH2:38][CH2:39][CH3:40].O>CN(C)C=O>[CH2:37]([NH:41][C:24](=[O:26])[N:23]([C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11](/[CH:10]=[C:4](\[O:3][CH2:1][CH3:2])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:12][CH:13]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:36])[CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 86626081ethyl (Z)-2-ethoxy-3-{3'-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate

Product 1

HCID 86626117ethyl (Z)-3-[3'-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.75 g (3 mmol) of ethyl (Z)-2-ethoxy-3-{3′-[methyl-(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate and 0.4 mL (3.7 mmol) of n-butylamine in 20 mL of dimethylformamide is heated at 80° C. for 2 hours. After addition of water, the reaction medium is extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 0.8 g (63%) of ethyl (Z)-3-[3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate is obtained in the form of a white solid after trituration from pentane.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-04b2bea031844ed297740e7c864ed326
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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