Benzocaine → HCID 71253061, compound

Temperature

80 °C

To 2-chloroethylamine hydrochloride (1.16 g) were added acetonitrile (15 mL) and sulfuryl chloride (6.08 mL), and the mixture was stirred at 80° C. for 8 hr. The solvent was evaporated from the reaction mixture, and to the obtained to residue was added tetrahydrofuran (10 mL). A solution of a mixture of ethyl 4-aminobenzoate (826 mg) and triethylamine (2.8 mL) in tetrahydrofuran (5 mL) was added dropwise under ice-cooling. The reaction mixture was stirred at room temperature overnight, and water was added. The mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was dissolved in dimethylsulfoxide (15 mL), potassium carbonate (1.38 g) was added, and the mixture was stirred at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (195 mg).

1. customThe solvent was evaporated from the reaction mixture
2. customto the obtained to residue
3. additionwas added dropwise under ice-
4. temperaturecooling
5. stirringThe reaction mixture was stirred at room temperature overnight
6. extractionThe mixture was extracted with ethyl acetate
7. customthe solvent was evaporated
8. dissolutionThe obtained residue was dissolved in dimethylsulfoxide (15 mL)
9. additionpotassium carbonate (1.38 g) was added
10. stirringthe mixture was stirred at room temperature
11. additionWater was added to the reaction mixture
12. extractionthe mixture was extracted with ethyl acetate
13. customthe solvent was evaporated
14. customThe obtained residue was purified by column chromatography (ethyl acetate:hexane)

ORD record

ord-0f5f514ca83440cd8bd0f0799d0e22fd

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816079B2