Triethylamine → HCID 772005, compound

To a stirred solution of 4-bromo-3-methylaniline (3.32 g, 17.8 mmol) in dry dichloromethane (150 ml) was added triethylamine (4.96 ml, 35.6 mmol), followed by methanesulphonyl chloride (1.52 ml, 19.6 mmol). The complete reaction mixture was stirred at room temperature under Ar for 18 hours. The mixture was then washed with water, saturated potassium carbonate solution, and finally brine. The organic layer was dried (Na2SO4) and concentrate din vacuo to afford a creamy orange solid. This was dissolved in dichloromethane and shaken with 10% sodium hydroxide solution. The aqueous layer was separated and acidified to pH 6 using concentrated hydrochloric acid. This solution was then extracted using chloroform. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford the title compound as a white solid (1.35 g, 30%).

1. washThe mixture was then washed with water, saturated potassium carbonate solution, and finally brine
2. dry with materialThe organic layer was dried (Na2SO4)
3. concentrationconcentrate din vacuo
4. customto afford a creamy orange solid
5. customThe aqueous layer was separated
6. extractionThis solution was then extracted
7. dry with materialThe combined organic layers were dried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-67b868cb1c474189bb977dc139c79949

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972951