n-Heptyl isocyanate → ethyl(E)-3-[5'-(3-heptyl-1-methylureido)-2'-methylbiphenyl-4-yl]acrylate

HRID 250864Notes

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

Participants

Conditions

Temperature: 50 °C

Procedure

660 μL (4.0 mmol, 1.5 eq) of heptyl isocyanate are added to a solution of 805 mg (2.72 mmol, 1 eq) of ethyl (E)-3-(2′-methyl-5′-methylaminobiphenyl-4-yl)acrylate in 8 mL of a 7/1 dichloromethane/triethylamine mixture. The reaction medium is stirred at 50° C. for 12 hours and then hydrolyzed with water and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residual oil is chromatographed on silica (7/3 heptane/ethyl acetate). 920 mg of ethyl (E)-3-[5′-(3-heptyl-1-methylureido)-2′-methylbiphenyl-4-yl]acrylate are obtained in oil form. Yield=77%

Workup

extractionhydrolyzed with water and extracted with ethyl acetate
washwashed with sodium chloride solution
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residual oil is chromatographed on silica (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-80d5395f5ee34e88a9f827a49a5a375f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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