Water → 4-octyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 1854291ノート

反応式

HRID 1854291 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH2:7]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].O>N1C=CC=CC=1>[CH2:7]([C:15]1[CH:16]=[CH:17][C:18]([S:21]([NH:1][C:2]2[S:3][CH:4]=[N:5][N:6]=2)(=[O:23])=[O:22])=[CH:19][CH:20]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

5

反応物 3

HCID 962WaterHCID 199091,3,4-Thiadiazol-2-amineHCID 11098208Benzenesulfonyl chloride, 4-octyl-

生成物 1

HCID 533184054-octyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide収率 55%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a stirred solution of 2-amino-1,3,4-thiadiazole (2.0 g, 19.7 mmol) in pyridine (30 mL) under argon at −20° C. was added p-octylbenzenesulfonyl chloride (6.06 g, 21 mmol) over 10 min. The reaction mixture was stirred at room temperature for 16 hours. Water (300 mL) was added to quench the reaction. The mixture was extracted with CH2Cl2 and the organic extracts washed with 2N HCl (2×150 mL), brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluted with methanol:DCM 1:33 to give the product (3.83 g, 10.8 mmol, 55% yield) as a solid, mp 123-124° C.; 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3H, J=7 Hz), 1.36 (m, 10H), 1.59 (m, 2H), 2.63 (t, 2H, J=7 Hz), 7.27 (d, 2H, J=8 Hz), 7.82 (d, 2H, J=8 Hz), 8.23 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 29.2, 29.3, 29.4, 31.1, 31.8, 35.9, 126.5, 129.0, 138.1, 142.6, 148.7, 167.3; MS (Q-TOF) Calcd for C16H24N3O2S2 354.1310, found 354.1211 (M+H)+; Calcd for C16H23N3N3O2S2 376.1129, found 376.1154 (M+Na)+.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic extracts washed with 2N HCl (2×150 mL), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluted with methanol:DCM 1:33

出典と根拠

ORDレコード
ord-bef9e6deb3914a8aa19aa778ebb99495
出典データセット
uspto-grants-2015_02
特許番号
US08962663B2

反応ノート

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