Reaction #2146759

Reaction equation

p-toluenesulfonylchloride

p-toluene-sulfonylchloride

(3-Chloro-4-fluoro-benzyl)-(2,2-dimethoxy-ethyl)-amine

pyridine

p-toluene-sulfonylchloride

→

title compound

Yield 65.0%

N-(3-Chloro-4-fluoro-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzene-sulfonamide

Yield 65.0%

Solvents

dichloromethane

dichloromethane pyridine

Conditions

Workup

1. 1
   Temperaturerefluxed for additional 4 h
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   WashFor workup, the solution was washed twice with 2 N HCl and twice with saturated NaHCO3-solution
4. 4
   DryingThe organic layer was dried with MgSO4
5. 5
   Otherevaporated

Procedure

147.0 g (3-Chloro-4-fluoro-benzyl)-(2,2-dimethoxy-ethyl)-amine (1, crude product) were dissolved in 540 ml of dichloromethane/pyridine (8:1). At 0° C. a solution of 145.8 g (1.04 mol) p-toluenesulfonylchloride in 200 ml of dichloromethane was added. After 5 h at room temperature additional 20 ml of pyridine, 29.16 g (0.15 mol) p-toluene-sulfonylchloride and a catalytic amount of DMAP were added. The solution was stirred at room temperature for 7 h and then refluxed for additional 4 h. Again 29.16 g (0.15 mol) p-toluene-sulfonylchloride and a catalytic amount of DMAP were added and the mixture was stirred overnight. For workup, the solution was washed twice with 2 N HCl and twice with saturated NaHCO3-solution. The organic layer was dried with MgSO4 and evaporated. Final silica gel chromatography (heptane/ethyl acetate 4:1) gave 155 g of the title compound as a yellow oil. Rt=1.80 min (Method B). Detected mass: 370.2 (M-OMe−).

Source