Réaction #2122519

Équation de réaction

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

Rendement 93.0%

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

Rendement 93.0%

Solvants

ethyl acetate

tetrahydrofuran

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added drop
2. 2
   AutreSolvents were removed by rotary evaporation
3. 3
   Autrethe residue thus obtained
4. 4
   Autrewas partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   LavageThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   Séchagedried over sodium sulfate
7. 7
   Autreevaporated
8. 8
   AutreThe oily residue thus obtained
9. 9
   TempératureThe mixture was cooled in the refrigerator overnight
10. 10
    Autrethe white solid that precipitated
11. 11
    Autrewas collected
12. 12
    Lavagewashed with hexane
13. 13
    Autredried

Mode opératoire

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:

Source