Water → ethyl (Z)-2-ethoxy-3-{3'-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate

HRID 390678Notes

Reaction equation

HRID 390678 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(NCC)C.[CH2:19]([O:21]/[C:22](=[CH:28]\[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([NH:41][CH3:42])[CH:36]=2)=[CH:31][CH:30]=1)/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:20].O>ClCCl>[CH2:19]([O:21]/[C:22](=[CH:28]\[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([N:41]([CH3:42])[C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH:36]=2)=[CH:31][CH:30]=1)/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 821294-Nitrophenyl chloroformateHCID 86626079ethyl (Z)-2-ethoxy-3-(3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 86626081ethyl (Z)-2-ethoxy-3-{3'-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylateYield 126.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.63 g (3.1 mmol) of 4-nitrophenyl chloroformate and then 0.54 mL (3.1 mmol) of diethylamine are added to a solution of 0.68 g (2.1 mmol) of ethyl (Z)-2-ethoxy-3-(3′-methylaminobiphenyl-4-yl)acrylate in 15 mL of dichloromethane. The reaction mixture is stirred for 1 hour 30 minutes at room temperature. The reaction is worked up by addition of 10 mL of water and then extracted with dichloromethane. The organic phases are combined and then dried over magnesium sulfate. The solvents are evaporated off. 1.3 g (100%) of ethyl (Z)-2-ethoxy-3-{3′-[methyl-(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate are obtained in the form of a yellow oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents are evaporated off

Sources & evidence

ORD record
ord-fa17fca0c2414bec984c3b6134d3eb22
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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