تفاعل #2487445

ord-0c926c8d6ef64ecdbf28f79a6b1d6755

معادلة التفاعل

O=S(=O)(Cl)c1ccc(F)c2n[se]nc12
7-fluoro-2,1,3-benzoselenadiazole-4-sulfonyl chloride
CCN(CC)CCN
N,N-diethylethylenediamine
CCN(CC)CC
triethylamine
CN(C)CCNS(=O)(=O)c1ccc(F)c2n[se]nc12
7-fluoro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoselenadiazole-4-sulfonamide
المردود 73.7%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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)+]

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08796037B2uspto-grants-2014_08