Water → HCID 54471286, compound

HRID 1900026Notes

Reaction equation

HRID 1900026 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18].C(OCC)(=O)C.O>C(Cl)Cl>[CH3:15][NH:16][C:17](=[O:18])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12228Methyl IsocyanateHCID 97826Ethyl 3-(4-aminophenyl)acrylate

Product 1

HCID 54471286HCID 54471286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-aminocinnamate (150 mg) in methylene chloride were added methyl isocyanate (0.06 ml) under nitrogen atmosphere at ambient temperature, and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with water twice, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized from diisopropyl ether to give ethyl 4-(3-methylureido)cinnamate (136 mg).

Workup

  1. washThe organic layer was washed with water twice
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3b22467e3aec434384ceb4eb717858d5
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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