Hydrochloric Acid → Carbamic acid, (4-mercaptophenyl)-, methyl ester

17.4 ml of a 10% aqueous sodium hydroxide solution were carefully added to 2.40 g of 4-aminothiophenol at room temperature and 3.27 ml of methyl chloroformate were added dropwise to the resulting mixture. The reaction mixture was then stirred at room temperature for 2 hours, at the end of which time the reaction mixture was acidified with 1.5 ml of 4N hydrochloric acid, and the resulting mixture was extracted with methylene: chloride. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude crystalline solid. 4 ml of methanol and 10 ml of a 2M solution of sodium methoxide in methanol were added to the crude crystalline solid at room temperature. The resulting mixture was then stirred at room temperature for 1.5 hours, at the end of which time the reaction mixture was acidified with 2 ml of 4N hydrochloric acid, and the resulting mixture was extracted with methylene chloride. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude crystalline residue which was recrystallised from a mixed solvent of methylene chloride and hexane to give 1.135 g (yield 32%) of the title compound as a solid having a melting point of 94° to 96° C.

1. extractionthe resulting mixture was extracted with methylene
2. extractionThe resulting extract
3. washwas washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was then removed by evaporation under reduced pressure
6. customto give a crude crystalline solid
7. stirringThe resulting mixture was then stirred at room temperature for 1.5 hours, at the end of which time the reaction mixture
8. extractionthe resulting mixture was extracted with methylene chloride
9. extractionThe resulting extract
10. washwas washed with water
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was then removed by evaporation under reduced pressure
13. customto give a crude crystalline residue which
14. customwas recrystallised from a mixed solvent of methylene chloride and hexane

ORD record

ord-3ff45f37c54342238f9295327936d8cd

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736487