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Water → ethyl (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate

HRID 390604
Notes
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Reaction equation

HRID 390604 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][C:12](=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH3:32])[CH:26]=2)=[CH:21][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)CC)C.O>ClCCl.C(OCC)(=O)C>[CH2:1]([NH:8][C:9](=[O:10])[N:31]([C:27]1[CH:26]=[C:25]([C:22]2[CH:23]=[CH:24][C:19](/[CH:18]=[C:12](\[CH3:11])/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:20][CH:21]=2)[CH:30]=[CH:29][CH:28]=1)[CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 138341n-Heptyl isocyanateHCID 68957155Ethyl 2-methyl-3-(3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 16225425ethyl (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylateYield 78.8%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

618 μL (3.8 mmol) of heptyl isocyanate are added to a solution of 750 mg (2.5 mmol) of ethyl 2-methyl-3-(3′-methylaminobiphenyl-4-yl)acrylate in 10 mL of dichloromethane in the presence of 2 mL of triethylamine. The reaction mixture is stirred for 12 hours at 50° C. The reaction is stopped by addition of 50 mL of water and extraction with ethyl acetate. The organic phases are washed with sodium chloride solution and dried over magnesium sulfate. The solvents are evaporated off, and the residue is then purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 860 mg (78%) of ethyl (E)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate are obtained.

Workup

  1. washThe organic phases are washed with sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then purified by chromatography on a column of silica
  5. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-cddd8ebdd087417d868302b7b74f5eb3
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383652B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes