Hydrochloric Acid → 4-Dodecyl-N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 1854269Notes

Reaction equation

HRID 1854269 reaction equation
[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:23][C:24]1[S:25][C:26]([CH2:29][OH:30])=[N:27][N:28]=1.Cl>N1C=CC=CC=1>[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:23][C:24]2[S:25][C:26]([CH2:29][OH:30])=[N:27][N:28]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 11062424(5-Amino-1,3,4-thiadiazol-2-yl)methanol

Product 1

HCID 529388564-Dodecyl-N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-dodecylbenzenesulfonyl chloride (200 mg, 0.58 mmol) in pyridine (3 mL) was added 2-amino-5-hydroxymethyl-1,3,4-thiadiazole (70 mg, 0.53 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (8 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×20 mL). The organic extracts were washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 19:1 to give the product as a solid, mp 138-139° C., in 65% yield (151 mg, 0.34 mmol); 1H NMR (300 MHz, DMSO-d6) δ 0.84 (t, 3H, J=6.6 Hz), 1.22 (m, 18H), 1.54-1.57 (m, 2H), 2.64 (t, 2H, J=7.8 Hz), 4.57 (s, 2H), 6.05 (br, 1H), 7.35 (d, 2H, J=8.1 Hz), 7.67 (d, 2H, J=7.8 Hz); 13C NMR (75 MHz, DMSO-d6) δ 13.9, 22.1, 28.6, 28.7, 28.8, 29.0, 30.6, 31.3, 34.9, 58.4, 125.8, 128.9, 139.2, 147.5, 161.1, 167.5; MS (LCQ, ESI+) Calcd for C21H34N3O3S2 440.2. found 440.2 (M+H)+; HRMS (ESI+, m/z) Calcd for C21H34N3O3S2 440.2042. found 440.2029 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe organic extracts were washed with water (10 mL), brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (70-230 mesh)
  9. washeluted with CH2Cl2:methanol 19:1

Sources & evidence

ORD record
ord-11ca3dc340074c46bb85c4ea3839d2e3
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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