반응 #2122519

반응 방정식

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

수율 93.0%

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

수율 93.0%

용매

ethyl acetate

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added drop
2. 2
   기타Solvents were removed by rotary evaporation
3. 3
   기타the residue thus obtained
4. 4
   기타was partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   세척The organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   건조dried over sodium sulfate
7. 7
   기타evaporated
8. 8
   기타The oily residue thus obtained
9. 9
   온도The mixture was cooled in the refrigerator overnight
10. 10
    기타the white solid that precipitated
11. 11
    기타was collected
12. 12
    세척washed with hexane
13. 13
    기타dried

실험 절차

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:

출처