Water → HCID 86676756, compound
Reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:19][CH2:20][CH2:21][CH2:22][N:23]=[C:24]=[O:25].O>ClCCl>[Cl:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:25])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethyl 4-aminobenzoate (496 mg) and pyridine (60 μL) was dissolved in dichloromethane (3 mL), 1-chloro-3-isocyanatopropane (323 μL) was added, and the mixture was stirred at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give ethyl 4-[3-(3-chloropropyl)ureido]benzoate (810 mg). The obtained ethyl 4-[3-(3-chloropropyl)ureido]benzoate (810 mg) was dissolved in N,N-dimethylformamide (10 mL), sodium hydride (250 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated from the organic layer. To the obtained residue was added diisopropyl ether, and the precipitate was collected by filtration to give the title compound (84 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with dilute hydrochloric acid and saturated brine
- customthe solvent was evaporated
- customThe obtained residue was purified by column chromatography (ethyl acetate:hexane)
Sources & evidence
- ORD record
- ord-7b7f6a0afab14feba746e4e02094571e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816079B2
Reaction notes
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