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

HRID 631070

Reaction equation

HRID 631070 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-9ba8aec8e2f74e20baf29c3825e8214b
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Linked notes

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