Hydrochloric Acid → Ethyl 5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate

HRID 1966904Notes

Reaction equation

HRID 1966904 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:28][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:26][N:25]=1.Cl>N1C=CC=CC=1>[C:1]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:23][C:24]2[S:28][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:26][N:25]=2)(=[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylateHCID 866543014-Decanamidobenzenesulfonyl chloride

Product 1

HCID 53318403Ethyl 5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-decanamidobenzenesulfonyl chloride (220 mg, 0.64 mmol) in pyridine (4 mL) was added ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (100 mg, 0.58 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (10 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 101-102° C., in 65% yield (183 mg, 0.38 mmol); 1H NMR (300 MHz, DMSO-d6) δ 0.83 (t, 3H, J=6.6 Hz), 1.22-1.32 (m, 15H), 1.56 (m, 2H), 2.31 (t, 2H, J=6.0 Hz), 4.33 (q, 2H, J=7.6 Hz), 7.71 (m, 4H), 10.19 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 14.6, 14.6, 22.8, 25.6, 29.3, 29.4, 29.5, 29.6, 31.3, 31.9, 37.1, 62.8, 119.1, 127.6, 136.8, 143.2, 147.7, 159.2, 170.3, 172.5; MS (LCQ, ESI+) Calcd for C21H31N4O5S2 483.2, found 483.1 (M+H)+; HRMS (ESI+, m/z) Calcd for C21H31N4O5S2 483.1736, found 483.1728 (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-cf701a9c6b5948aea9d87935988dc05c
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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