n-Heptyl isocyanate → Ethyl 2-[1-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(e)-ylidene]pentanoate
Reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[C:26](\[CH2:32][CH2:33][CH3:34])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1>>[CH2:1]([NH:8][C:9](=[O:10])[N:12]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[C:26](\[CH2:32][CH2:33][CH3:34])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
172 μL (1 mmol) of heptyl isocyanate are added to 251 mg (0.8 mmol) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]pentanoate (prepared according to Example 8a). The reaction mixture is heated at 100° C. in an Emrys Optimizer microwave oven for 20 minutes. The residue is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 361 mg (100%) of ethyl 2-[1-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]pentanoate are obtained in the form of a yellowish oil.
Workup
- customThe residue is purified by chromatography on a column of silica
- washeluted with a 70/30 heptane/ethyl acetate mixture
Sources & evidence
- ORD record
- ord-6e2037cd9b214b8abc18800156358393
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383652B2
Reaction notes
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