N-Benzylethylenediamine → 2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide

HRID 560550

反応式

HRID 560550 の反応式
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12](N)(N)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][S:12]1(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 77801N-BenzylethylenediamineHCID 82267Sulfamide

生成物 1

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide収率 40%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of N-benzylethane-1,2-diamine (1.00 g, 6.65 mmol) in pyridine (10 mL) was added sulfamide (0.77 g, 7.98 mmol). The mixture was refluxed for 16 hours. The solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/4) to afford the title compound as an oily solid in 40% yield (0.57 g): 1H NMR (300 MHz, CDCl3) δ 7.35-7.27 (m, 5H), 4.59 (br s, 1H), 4.15 (s, 2H), 3.48-3.42 (m, 2H), 3.27-3.22 (m, 2H); MS (ES+) m/z 213.2 (M+1).

後処理

  1. temperatureThe mixture was refluxed for 16 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with water (200 mL) and brine (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with ethyl acetate/hexane (1/4)

出典と根拠

ORDレコード
ord-e14c6f0b0c3943e1a443ce0b6e6e5565
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

関連ノート

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