n-Heptyl isocyanate → Ethyl 2-[1-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrate

HRID 390607Notes

Reaction equation

HRID 390607 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][CH3:33])/[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][CH3:33])/[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

Reactant 2

HCID 138341n-Heptyl isocyanateHCID 68962496Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate

Product 1

HCID 68958165Ethyl 2-[1-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrateYield 98%

Conditions

Temperature
100 °C

Procedure

172 μL (1 mmol) of heptyl isocyanate are added to 214 mg (0.7 mmol) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]butyrate. 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. 306 mg (98%) of ethyl 2-[1-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate are obtained in the form of yellowish crystals.

Workup

  1. customThe residue is purified by chromatography on a column of silica
  2. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-7dc91c9ac733418f8cf49f1abaa4cf47
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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