Hydrochloric Acid → 4-octadecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 631080Notes

Reaction equation

HRID 631080 reaction equation
[CH2:1]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[S:29]1[CH:33]=[N:32][N:31]=[C:30]1[NH2:34].Cl>N1C=CC=CC=1>[CH2:1]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:34][C:30]2[S:29][CH:33]=[N:32][N:31]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199091,3,4-Thiadiazol-2-amineHCID 15597598p-Octadecylbenzenesulfonyl chloride

Product 1

HCID 533223764-octadecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 51.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-octadecylbenzenesulfonyl chloride (500 mg, 1.17 mmol) in pyridine (8 mL) was added 1,3,4-thiadiazol-2-amine (177 mg, 1.75 mmol). The reaction mixture was stirred at room temperature for 6 hours, then 2 M HCl (40 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×50 mL), the organic layer was washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with methanol:DCM 1:19 to give the product as a solid (296 mg, 0.60 mmol, 51% yield), mp 116-117° C.; 1H NMR (300 MHz, CDCl3) δ 0.86 (t, 3H, J=6.9 Hz), 1.25 (m, 30H), 1.60 (m, 2H), 2.64 (t, 2H, J=7.8 Hz), 7.29 (d, 2H, J=7.8 Hz), 7.82 (d, 2H, J=7.8 Hz), 8.21 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.0, 22.7, 29.2, 29.3, 29.4, 29.5, 29.6, 29.7, 31.1, 31.9, 35.9, 126.5, 128.9, 138.1, 142.6, 148.6, 167.4; MS (LCQ, ESI+) Calcd for C26H44N3O2S2 494.3. found 494.2 (M+H)+. HRMS (ESI+, m/z) Calcd for C26H44N3O2S2 494.2869. found 494.2869 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washthe organic layer was washed with water (40 mL) and brine (40 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography over silica gel (70-230 mesh)
  8. washeluted with methanol:DCM 1:19

Sources & evidence

ORD record
ord-700e706b7f6c48cab6aa6eff51aa4e10
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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