Reaktion #2122519

Reaktionsgleichung

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

Ausbeute 93.0%

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

Ausbeute 93.0%

Lösungsmittel

ethyl acetate

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added drop
2. 2
   SonstigeSolvents were removed by rotary evaporation
3. 3
   Sonstigethe residue thus obtained
4. 4
   Sonstigewas partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   WaschenThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   Trocknendried over sodium sulfate
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe oily residue thus obtained
9. 9
   TemperaturThe mixture was cooled in the refrigerator overnight
10. 10
    Sonstigethe white solid that precipitated
11. 11
    Sonstigewas collected
12. 12
    Waschenwashed with hexane
13. 13
    Sonstigedried

Vorschrift

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:

Quelle