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

HRID 631074노트

반응식

HRID 631074 반응식
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH2:7]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O>N1C=CC=CC=1>[CH2:7]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:1][C:2]2[S:3][CH:4]=[N:5][N:6]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

5

반응물 3

HCID 962WaterHCID 199091,3,4-Thiadiazol-2-amineHCID 125827864-Hexylbenzene-1-sulfonyl chloride

생성물 1

HCID 533223754-hexyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide수율 58%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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-hexylbenzenesulfonyl chloride (5.48 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 (3.72 g, 11.4 mmol, 58% yield) as a solid, mp 125-126° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=7 Hz), 1.28 (m, 6H), 1.58 (m, 2H), 2.63 (t, 2H, J=7 Hz), 7.27 (d, 2H, J=8 Hz), 7.83 (d, 2H, J=8 Hz), 8.24 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 28.9, 31.1, 31.6, 35.9, 126.5, 129.0, 138.1, 142.6, 148.6, 167.4; MS (Q-TOF) Calcd for C14H20N3O2S2 326.0997. found 326.0931 (M+H)+. Calcd for C14H19N3NaO2S2 348.0816. found 348.0816 (M+Na)+.

후처리

  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

출처 및 근거

ORD 기록
ord-029cb75d073b467291ce670adaf83c42
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320734B2

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