Dimethylamine → N,N,2-trimethylbenzo[d]thiazole-6-sulfonamide

A solution of Compound 2 (5.0 g, 20.2 mmol) from step (b) of Example 1 dissolved in tetrahydrofuran (THF, 30 ml) was added drop wise to a mixture of 2M N,N-dimethyl amine in THF (12 mL, 24.2 mmol) and triethylamine (5.6 ml, 40.4 mmol). The resultant mixture was stirred at room temperature for 3 hours. Solvents were removed by rotary evaporation and the residue thus obtained was partitioned between chloroform (100 ml) and water (100 ml). The organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml), dried over sodium sulfate and evaporated. The oily residue thus obtained was dissolved in ca. 5 ml of hot ethyl acetate and this solution was then slowly added to 45 ml hexane. The mixture was cooled in the refrigerator overnight and the white solid that precipitated was collected, washed with hexane and dried to yield 4.8 g (93%) of Compound 24 whose structure is given below:

1. additionwas added drop
2. customSolvents were removed by rotary evaporation
3. customthe residue thus obtained
4. customwas partitioned between chloroform (100 ml) and water (100 ml)
5. washThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. dry with materialdried over sodium sulfate
7. customevaporated
8. customThe oily residue thus obtained
9. temperatureThe mixture was cooled in the refrigerator overnight
10. customthe white solid that precipitated
11. customwas collected
12. washwashed with hexane
13. customdried

ORD record

ord-4ac7c52dee7b4688b920d3754a450e92

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759526B2