Reaction #2487445

Reaction equation

7-fluoro-2,1,3-benzoselenadiazole-4-sulfonyl chloride

N,N-diethylethylenediamine

triethylamine

→

7-fluoro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoselenadiazole-4-sulfonamide

Yield 73.7%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe reaction mixture was evaporated to dryness in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   Otherchromatographed on silica gel

Procedure

7-fluoro-2,1,3-benzoselenadiazole-4-sulfonyl chloride (75 mg) was dissolved in 3 ml of acetonitrile. After the addition of N,N-diethylethylenediamine (22 mg) and triethylamine (351), the mixture was stirred on ice for 30 min. The reaction mixture was evaporated to dryness in vacuo and the residue was dissolved in CH2Cl2 and chromatographed on silica gel using CH2Cl2-CH3OH (93:7) to yield 7-fluoro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoselenadiazole-4-sulfonamide (49 mg, 56%) as red powder. mp: 117-120° C. 1H-NMR δH8.09 (1H, d, J=7.5 Hz), 7.24 (1H, d, J=7.5 Hz), 2.93 (2H, t, J=6.7 Hz), 2.27 (2H, t, J=6.7 Hz), 1.98 (6H, s) in CD3OD; ESI-MSm/z 353 [(M+H)+]

Source