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

HRID 631047Notes

Reaction equation

HRID 631047 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH3:8])=[N:5][N:6]=1.[CH2:9]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>N1C=CC=CC=1>[CH2:9]([C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:1][C:2]2[S:3][C:4]([CH2:7][CH3:8])=[N:5][N:6]=2)(=[O:29])=[O:28])=[CH:25][CH:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 264442-Amino-5-ethyl-1,3,4-thiadiazoleHCID 1042154-Dodecylbenzenesulfonyl chloride

Product 1

HCID 533197364-dodecyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

2-Amino-5-ethyl-1,3,4-thiadiazole (169 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 (225 mg, 0.51 mmol, 59%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 93-94° C.; 1H NMR (500 MHz, CDCl3) δ 0.88 (3, t, J=6.5 Hz), 1.20-1.36 (18, m), 1.33 (3, t, J=7.5 Hz), 1.54-1.63 (2, m), 2.63 (2, t, J=7.5 Hz), 2.84 (2, q, J=7.5 Hz), 7.25 (2, d, J=8.5 Hz), 7.83 (2, d, J=8.5 Hz), 12.30 (1, br s); 13C NMR (125 MHz, CDCl3) δ 12.6, 14.1, 22.7, 24.4, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 126.5, 128.8, 138.4, 148.2, 160.1 168.2; MS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2249. found 438.30 (M+H)+. HRMS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2249. found 438.2247 (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-2da80c6780734deaad1059f58dbd5dfe
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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