Water → HCID 54471286, compound

HRID 1290211Notes

Reaction equation

HRID 1290211 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-1dc47818930e4267b98941eaa85f63cb
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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