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

HRID 390604Notes

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]

Participants

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

washThe organic phases are washed with sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvents are evaporated off
customthe residue is then purified by chromatography on a column of silica
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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