Reaction #2122517

Reaction equation

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

dihexylamine

hexane

→

Compound 20

Yield 97.0%

N,N-dihexyl-2-methylbenzo[d]thiazole-6-sulfonamide

Yield 97.0%

Solvents

ethyl acetate

chloroform

chloroform

Conditions

Workup

1. 1
   WashThe reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml)
2. 2
   DryingThe organic layer was then dried with sodium sulfate
3. 3
   Otherevaporated
4. 4
   OtherThe residue thus obtained
5. 5
   OtherThe white solid that precipitated
6. 6
   Filtrationwas filtered
7. 7
   Otherthe filtrate evaporated to dryness

Procedure

A solution of Compound 2 (5.0 g, 20.2 mmol) from step (b) of Example 1 dissolved in chloroform (30 ml) was added drop wise to a solution of dihexylamine (4.5 g, 24.2 mmol) in chloroform (20 ml). The combined mixture was stirred at room temperature for 2 hours. The reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml). The organic layer was then dried with sodium sulfate and evaporated. The residue thus obtained was suspended in ca. 5 ml hot ethyl acetate and this solution was then slowly added to 40 ml hexane. The white solid that precipitated was filtered and the filtrate evaporated to dryness to provide 7.76 g (97%) of Compound 20 as a syrupy liquid, Rf=0.43 (30% ethyl acetate in hexane). The structure of this compound is given below:

Source