4-(Trifluoromethyl)phenyl isocyanate → ethyl (Z)-2-ethoxy-3-{3'-[1-methyl-3-(4-trifluoromethylphenyl)ureido]biphenyl-4-yl}acrylate

HRID 390687Notes

Reaction equation

HRID 390687 reaction equation
[CH2:1]([O:3]/[C:4](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH3:24])[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>>[CH2:1]([O:3]/[C:4](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:24])[C:34]([NH:33][C:30]3[CH:29]=[CH:28][C:27]([C:26]([F:36])([F:37])[F:25])=[CH:32][CH:31]=3)=[O:35])[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 86626079ethyl (Z)-2-ethoxy-3-(3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 86626120ethyl (Z)-2-ethoxy-3-{3'-[1-methyl-3-(4-trifluoromethylphenyl)ureido]biphenyl-4-yl}acrylateYield 97.6%

Conditions

Temperature
50 °C

Procedure

A mixture of 1 g (3 mmol) of ethyl (Z)-2-ethoxy-3-(3′-methylaminobiphenyl-4-yl)acrylate (prepared according to Example 43b) and 0.8 mL (6 mmol) of 4-trifluoromethylphenyl isocyanate is placed in a sealed tube and heated at 50° C. for 15 hours. The reaction medium is cooled and the residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 1.5 g (95%) of ethyl (Z)-2-ethoxy-3-{3′-[1-methyl-3-(4-trifluoromethylphenyl)ureido]biphenyl-4-yl}acrylate are obtained in the form of a white foam.

Workup

  1. customis placed in a sealed tube
  2. temperatureThe reaction medium is cooled
  3. customthe residue obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-239500d77cb84b87a892b62ac9eee2c6
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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