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

HRID 1966907

반응식

HRID 1966907 반응식
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH2:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].O>N1C=CC=CC=1>[CH2:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:1][C:2]2[S:3][CH:4]=[N:5][N:6]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10]

참가 물질

5

반응물 3

HCID 962WaterHCID 199091,3,4-Thiadiazol-2-amineHCID 27373524-Butylbenzene-1-sulfonyl chloride

생성물 1

HCID 533237344-butyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide수율 59%

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-butylbenzenesulfonyl chloride (4.89 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 (3.46 g, 11.6 mmol, 59% yield) as a solid, mp 120-121° C.; 1H NMR (300 MHz, CDCl3) δ 0.91 (t, 3H, J=7 Hz), 1.29-1.37 (m, 2H), 1.56-1.61 (m, 2H), 2.65 (t, 2H, J=7 Hz), 7.27 (d, 2H, J=8 Hz), 7.84 (d, 2H, J=8 Hz), 8.25 (s, 1H); 13C NMR (75 MHz, CDCl3) 13.9, 22.3, 33.2, 33.6, 126.5, 129.1, 138.1, 142.7, 148.6, 167.4; MS (Q-TOF) Calcd for C12H16N3O2S2 298.0684, found 298.0695 (M+H)+; Calcd for C12H15N3NaO2S2 320.0503, found 320.0361 (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-221916d4686e4464a83d9c6182c58a94
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420678B2

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