Water → HCID 71252167, compound

HRID 2411184Notes

Reaction equation

HRID 2411184 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:19])[NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.[H-].[Na+].O>CN(C)C=O>[O:19]=[C:6]1[NH:5][CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86676756HCID 86676756, compound

Product 1

HCID 71252167HCID 71252167, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customthe solvent was evaporated from the organic layer
  4. additionTo the obtained residue was added diisopropyl ether
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-655f855c18ac4c7e9c521b25164c9d97
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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