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

HRID 1854297Notes

Reaction equation

HRID 1854297 reaction equation
[CH2:1]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=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][CH3:16].[S:27]1[CH:31]=[N:30][N:29]=[C:28]1[NH2:32].Cl>N1C=CC=CC=1>[CH2:1]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:32][C:28]2[S:27][CH:31]=[N:30][N:29]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=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][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199091,3,4-Thiadiazol-2-amineHCID 20570237p-Hexadecylbenzenesulfonyl chloride

Product 1

HCID 529388554-hexadecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-hexadecylbenzenesulfonyl chloride (600 mg, 1.50 mmol) in pyridine (8 mL) was added 1,3,4-thiadiazol-2-amine (228 mg, 2.25 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 (320 mg, 0.69 mmol, 46% yield), mp 118-119° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=6.9 Hz), 1.25 (m, 26H), 1.59 (m, 2H), 2.64 (t, 2H, J=8.1 Hz), 7.29 (d, 2H, J=7.8 Hz), 7.84 (d, 2H, J=7.8 Hz), 8.23 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.7, 29.2, 29.3, 29.4, 29.6, 29.7, 31.1, 31.9, 35.9, 126.5, 128.9, 138.1, 142.5, 148.7, 167.5; MS (LCQ, ESI+) Calcd for C24H40N3O2S2 466.3, found 466.3 (M+H)+; HRMS (ESI+, m/z) Calcd for C24H40N3O2S2 466.2556, found 466.2558 (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-ab4937a9a84f4ff188cf2a72be8d72b7
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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