Reaction #1106685

Reaction equation

Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine

triethylamine

dimethylsulfamoyl chloride

→

title compound

N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N′,N′dimethylsulfamide

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe reaction mixture was partitioned between ethyl acetate and water
3. 3
   Washthe ethyl acetate solution was washed with brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Otherevaporated in vacuo
6. 6
   Otherto yield an oil
7. 7
   OtherThe oil was purified
8. 8
   Otherto yield a white solid, which
9. 9
   Otherwas recrystallized (ethyl acetate/Hexane)

Procedure

Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane—1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid.

Source