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

HRID 631076Notes

Reaction equation

HRID 631076 reaction equation
[CH2:1]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=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][CH3:14].[S:25]1[CH:29]=[N:28][N:27]=[C:26]1[NH2:30].Cl>N1C=CC=CC=1>[CH2:1]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:30][C:26]2[S:25][CH:29]=[N:28][N:27]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=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][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199091,3,4-Thiadiazol-2-amineHCID 15715900p-Tetradecylbenzenesulfonyl chloride

Product 1

HCID 529388544-tetradecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-tetradecylbenzenesulfonyl chloride (440 mg, 1.18 mmol) in pyridine (8 mL) was added 1,3,4-thiadiazol-2-amine (179 mg, 1.77 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 (240 mg, 0.55 mmol, 47% yield), mp 116-117° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=6.9 Hz), 1.25 (m, 22H), 1.60 (m, 2H), 2.64 (t, 2H, J=7.2 Hz), 7.29 (d, 2H, J=8.4 Hz), 7.84 (d, 2H, J=8.4 Hz), 8.23 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 126.5, 128.9, 138.1, 142.6, 148.6, 167.4; MS (LCQ, ESI+) Calcd for C22H36N3O2S2 438.2. found 438.3 (M+H)+. HRMS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2243. found 438.2243 (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-95d38658ba0b42e7acb6048e0c6bb400
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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