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

HRID 631072Notes

Reaction equation

HRID 631072 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

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-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 C16H23N3NaO2S2 376.1129. found 376.1154 (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-072e277d03fb4ce8bf7689403128fea0
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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