Реакция #2122519

Уравнение реакции

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

Выход 93.0%

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

Выход 93.0%

Растворители

ethyl acetate

tetrahydrofuran

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added drop
2. 2
   ДругоеSolvents were removed by rotary evaporation
3. 3
   Другоеthe residue thus obtained
4. 4
   Другоеwas partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   ПромывкаThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   Сушкаdried over sodium sulfate
7. 7
   Другоеevaporated
8. 8
   ДругоеThe oily residue thus obtained
9. 9
   ТемператураThe mixture was cooled in the refrigerator overnight
10. 10
    Другоеthe white solid that precipitated
11. 11
    Другоеwas collected
12. 12
    Промывкаwashed with hexane
13. 13
    Другоеdried

Методика

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:

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