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

HRID 1966903Notes

Reaction equation

HRID 1966903 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:15][C:16]1[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:18][N:17]=1.Cl>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][C:16]2[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:18][N:17]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8481N-Acetylsulfanilyl chlorideHCID 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 53322374Ethyl 5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-acetamidobenzenesulfonyl chloride (1.98 g, 8.47 mmol) in pyridine (20 mL) was added ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (1.2 g, 7.06 mmol). The reaction mixture was stirred at room temperature for 4.5 h, than 2 M HCl (50 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×60 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 19:1 to give the product as a solid, mp 201-202° C., in 73% yield (1.91 g, 5.15 mmol); 1H NMR (300 MHz, DMSO-d6) δ 1.29 (t, 3H, J=6.9 Hz), 2.08 (s, 3H), 4.37 (q, 2H, J=7.8 Hz), 7.74 (m, 4H), 10.32 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 13.9, 14.0, 24.1, 62.9, 118.6, 127.1, 134.9, 143.2, 147.2, 157.5, 167.6, 169.0; MS (LCQ, ESI+) Calcd for C13H15N4O5S2 371.0, found 371.0 (M+H)+; HRMS (ESI+, m/z) Calcd for C13H15N4O5S2 371.0484, found 371.0472 (M+H)+.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate (3×60 mL)
  5. washThe organic extracts were washed with water (50 mL), brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (70-230 mesh)
  10. washeluted with CH2Cl2:methanol 19:1

Sources & evidence

ORD record
ord-dc4f7322d2d9497b8b9d12d6fb0b4575
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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