Reacción #2122519

Ecuación de reacción

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

Rendimiento 93.0%

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

Rendimiento 93.0%

Disolventes

ethyl acetate

tetrahydrofuran

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added drop
2. 2
   OtroSolvents were removed by rotary evaporation
3. 3
   Otrothe residue thus obtained
4. 4
   Otrowas partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   LavadoThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   Secadodried over sodium sulfate
7. 7
   Otroevaporated
8. 8
   OtroThe oily residue thus obtained
9. 9
   TemperaturaThe mixture was cooled in the refrigerator overnight
10. 10
    Otrothe white solid that precipitated
11. 11
    Otrowas collected
12. 12
    Lavadowashed with hexane
13. 13
    Otrodried

Procedimiento

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:

Fuente