Reaction #2122519

Reaction equation

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

N,N-dimethyl amine

triethylamine

hexane

→

Compound 24

Yield 93.0%

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

Yield 93.0%

Solvents

ethyl acetate

tetrahydrofuran

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added drop
2. 2
   OtherSolvents were removed by rotary evaporation
3. 3
   Otherthe residue thus obtained
4. 4
   Otherwas partitioned between chloroform (100 ml) and water (100 ml)
5. 5
   WashThe organic layer was then washed with water (2×, 100 ml) and brine (1×, 100 ml)
6. 6
   Dryingdried over sodium sulfate
7. 7
   Otherevaporated
8. 8
   OtherThe oily residue thus obtained
9. 9
   TemperatureThe mixture was cooled in the refrigerator overnight
10. 10
    Otherthe white solid that precipitated
11. 11
    Otherwas collected
12. 12
    Washwashed with hexane
13. 13
    Otherdried

Procedure

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