Water → ethyl (Z)-2-ethoxy-3-[3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]acrylate

HRID 390613Notes

Reaction equation

HRID 390613 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](OC3C=CC([N+]([O-])=O)=CC=3)=[O:25])[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH2:37]([NH2:45])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.O>CN(C)C=O>[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]([NH:45][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:25])[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1001PhenethylamineHCID 86626081ethyl (Z)-2-ethoxy-3-{3'-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate

Product 1

HCID 86626080ethyl (Z)-2-ethoxy-3-[3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]acrylateYield 50%

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, 0.46 mL (3.7 mmol) of phenethylamine, 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. 0.7 g (50%) of ethyl (Z)-2-ethoxy-3-[3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]acrylate is obtained.

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-d8f747ed31024dc48323d038ea65c181
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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