反応 #2122519

反応方程式

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

収率 93.0%

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

収率 93.0%

溶媒

ethyl acetate

tetrahydrofuran

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added drop
2. 2
   その他Solvents were removed by rotary evaporation
3. 3
   その他the residue thus obtained
4. 4
   その他was partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   洗浄The organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   乾燥dried over sodium sulfate
7. 7
   その他evaporated
8. 8
   その他The oily residue thus obtained
9. 9
   温度The mixture was cooled in the refrigerator overnight
10. 10
    その他the white solid that precipitated
11. 11
    その他was collected
12. 12
    洗浄washed with hexane
13. 13
    その他dried

実験手順

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:

出典