4-Methylphenyl isocyanate → ethyl (Z)-2-ethoxy-3-[3'-(1-methyl-3-p-tolylureido)biphenyl-4-yl]acrylate

HRID 390686Notes

Reaction equation

HRID 390686 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].[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=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:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([CH3:25])=[CH:27][CH:28]=3)=[O:34])[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 693254-Methylphenyl isocyanateHCID 86626079ethyl (Z)-2-ethoxy-3-(3'-methylaminobiphenyl-4-yl)acrylate

Product 1

HCID 86626119ethyl (Z)-2-ethoxy-3-[3'-(1-methyl-3-p-tolylureido)biphenyl-4-yl]acrylateYield 87.2%

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 41b) and 0.8 mL (6 mmol) of 4-methylphenyl 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. 1.2 g (85%) of ethyl (Z)-2-ethoxy-3-[3′-(1-methyl-3-p-tolylureido)biphenyl-4-yl]acrylate are obtained in the form of a white paste.

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-2ab0a22183eb40c99a8d281ed6ecc1b9
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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