Pentane, 1-isocyanato- → Ethyl 2-[1-[3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrate

HRID 390610Notes

Reaction equation

HRID 390610 reaction equation
[CH2:1]([N:6]=[C:7]=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:9][NH:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[CH2:30][CH3:31])/[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1>>[CH2:1]([NH:6][C:7](=[O:8])[N:10]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[CH2:30][CH3:31])/[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:9])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 206036Pentane, 1-isocyanato-HCID 68962496Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate

Product 1

HCID 68958868Ethyl 2-[1-[3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrateYield 100%

Conditions

Temperature
100 °C

Procedure

136 μL (1.0 mmol) of pentyl isocyanate are added to 213 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. 291 mg (100%) of ethyl 2-[1-[3′-(3-pentyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate are obtained in the form of a yellowish oil.

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-127fbbecc563407dba27fec20633eb8a
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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