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

HRID 631046Notes

Reaction equation

HRID 631046 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[CH2:8]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>N1C=CC=CC=1>[CH2:8]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C:2]2[S:3][C:4]([CH3:7])=[N:5][N:6]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 1042154-Dodecylbenzenesulfonyl chloride

Product 1

HCID 533223774-dodecyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

2-Amino-5-methyl-1,3,4-thiadiazole (150 mg, 1.3 mmol) was suspended in pyridine (0.5 mL). p-Dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred at this temperature for 1 h. The reaction mixture was then added to aqueous 10% HCl (5 mL) and the resulting mixture extracted with ethyl acetate (3×10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2 gave the product (310 mg, 0.73 mmol, 84%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 149-150° C.; 1H NMR (500 MHz, CDCl3) δ 0.88 (3, t, J=7.0 Hz), 1.20-1.36 (18, m), 1.54-1.63 (2, m), 2.51 (3, s), 2.63 (2, t, J=7.5 Hz), 7.25 (2, d, J=7.5 Hz), 7.83 (2, d, J=7.5 Hz), 12.36 (1, br s); 13C NMR (125 MHz, CDCl3) δ 14.1, 16.5, 22.7, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 126.4, 128.8, 138.3, 148.3, 154.1, 168.6; MS (ESI+, m/z) Calcd for C21H34N3O2S2 424.2092. found 424.20 (M+H)+. HRMS (ESI+, m/z) Calcd for C21H34N3O2S2 424.2092. found 424.2085 (M+H)+.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (3×10 mL)
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customvolatiles evaporated
  6. customto yield a solid mass
  7. washChromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-55666410a8bc455b8d621e7199b76763
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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