Phenyl isocyanate → Methyl 3-[2-(3-phenylureido)phenyl]acrylate

HRID 916728Notes

Reaction equation

HRID 916728 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[O:7].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[C:14]1([NH:20][C:21](=[O:22])[NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[O:7])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 53439609Methyl 2-aminocinnamate

Product 1

HCID 69478288Methyl 3-[2-(3-phenylureido)phenyl]acrylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 2-aminocinnamate (2) (6.35 g, 35.8 mmol) was dissolved in 150 ml of benzene and phenylisocyanate (5.12 g, 43.0 mmol) was slowly dropped thereto at a room temperature. The reaction mixture was stirred for 12 hours to obtain a solid precipitate. Then, the precipitate was washed with ether in order to obtain the title compound (3) in the form of a white crystal (10.2 g, 96%) (mp 184° C.).

Workup

  1. customat a room temperature
  2. customto obtain a solid precipitate
  3. washThen, the precipitate was washed with ether in order

Sources & evidence

ORD record
ord-da717c1802c8431abad48c54765181fc
Source dataset
uspto-grants-2007_09
Patent number
US07271260B2

Reaction notes

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