Hydrochloric Acid → N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide

HRID 1966905Notes

Reaction equation

HRID 1966905 reaction equation
[C:1]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:23][C:24]1[S:25][C:26]([CH2:29][OH:30])=[N:27][N:28]=1.Cl>N1C=CC=CC=1>[OH:30][CH2:29][C:26]1[S:25][C:24]([NH:23][S:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[N:28][N:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11062424(5-Amino-1,3,4-thiadiazol-2-yl)methanolHCID 866543014-Decanamidobenzenesulfonyl chloride

Product 1

HCID 53323733N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamideYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-decanamidobenzenesulfonyl chloride (435 mg, 1.26 mmol) in pyridine (5 mL) was added 2-amino-5-hydroxymethyl-1,3,4-thiadiazole (150 mg, 1.15 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (15 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×30 mL). The organic extracts were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 9:1 to give the product as a solid, mp 69-70° C., in 73% yield (370 mg, 0.84 mmol); 1H NMR (300 MHz, DMSO-d6) δ 0.84 (t, 3H, J=7.2 Hz), 1.23 (m, 12H), 1.54-1.57 (m, 2H), 2.29 (t, 2H, J=7.5 Hz), 4.57 (d, 2H, J=4.8 Hz), 6.08 (t, 1H, J=5.0 Hz), 7.73 (m, 4H), 10.22 (s, 1H), 14.01 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 14.6, 22.8, 25.6, 30.0, 29.4, 29.5, 29.6, 31.9, 37.1, 59.1, 119.3, 127.6, 136.1, 143.5, 161.7, 168.1, 172.6; MS (LCQ, ESI+) Calcd for C19H29N4O4S2 441.2, found 441.1 (M+H)+; HRMS (ESI+, m/z) Calcd for C19H29N4O4S2 441.1630, found 441.1624 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  4. washThe organic extracts were washed with water (20 mL), brine (20 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 9:1

Sources & evidence

ORD record
ord-18f3fb3dec364839bd46a17383c7caf8
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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