Hydrochloric Acid → N-(5-(5-Bromopentyl)-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide

HRID 1854303Notes

Reaction equation

HRID 1854303 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].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[S:33][C:32]([NH2:34])=[N:31][N:30]=1.Cl>N1C=CC=CC=1>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[S:33][C:32]([NH:34][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[N:31][N:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 199329325-(5-Bromopentyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 66642947N-(5-(5-Bromopentyl)-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamideYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-dodecylbenzenesulfonyl chloride (1.53 g, 4.42 mmol) in pyridine (15 mL) was added 5-(5-bromopentyl)-1,3,4-thiadiazol-2-amine. (1.00 g, 4.02 mmol). The reaction mixture was stirred at room temperature for 5 h, then 2 mol/L HCl (25 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×50 mL). The organic extracts were washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography over silica gel 60 (70-230 mesh) eluted with CH2Cl2:MeOH 49:1 to give 1.39 g of product as a solid contaminated with N-(5-(5-chloropentyl)-1,3,4-thiadiazol-2-yl)-4-dodecyl benzenesulfonamide in about 60% yield. 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3, J=6.9 Hz), 1.25-1.30 (m, 18), 1.55-1.58 (m, 4), 1.73-1.88 (m, 4), 2.64 (t, 2, J=7.8 Hz), 2.83 (t, 2, J=7.8 Hz), 3.42 (t, 1, J=6.6), 3.55 (t, 1, J=6.3 Hz), 7.27 (d, 2, J=8.1 Hz), 7.84 (d, 2, J=8.1 Hz); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.6, 26.0, 27.3, 27.4, 27.5, 29.3, 29.4, 29.5, 29.6, 29.7, 30.5, 31.1, 31.8, 31.9, 32.0, 33.2, 35.8, 44.5, 126.5, 128.9, 138.3, 148.3, 158.5, 168.2; HRMS (ESI+, m/z) calculated for C25H41BrN3O2S2 558.1824, observed 558.1819 (M+H)+; HRMS (ESI+, m/z) calculated for C25H41ClN3O2S2 514.2329, observed 514.2330 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe organic extracts were washed with water (50 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography over silica gel 60 (70-230 mesh)
  9. washeluted with CH2Cl2:MeOH 49:1

Sources & evidence

ORD record
ord-0d07852c7ada492685e5e077e610c403
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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