Hydrochloric Acid → Ethyl 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate

HRID 1966895Notes

Reaction equation

HRID 1966895 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]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[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]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[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 292304Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate

Product 1

HCID 53323731Ethyl 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetateYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-acetamidobenzenesulfonyl chloride (275 mg, 1.18 mmol) in pyridine (5 mL) was added ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate (200 mg, 1.07 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 (3×50 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 over silica gel (70-230 mesh) eluted with CH2Cl2:methanol 19:1 to give the product as a solid, mp 156-157° C., in 76% yield (312 mg, 0.81 mmol); 1H NMR (300 MHz, DMSO-d6) δ 1.20 (t, 3H, J=7.0 Hz), 2.07 (s, 3H), 4.06 (s, 2H), 4.15 (q, 2H, J=7.0 Hz), 7.72 (m, 4H), 10.29 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 14.0, 24.1, 35.7, 61.3, 118.6, 127.0, 135.5, 142.9, 151.6, 167.8, 168.1, 169.0; MS (LCQ, ESI+) Calcd for C14H17N4O5S2 385.1, found 385.1 (M+H)'; HRMS (ESI+, m/z) Calcd for C14H17N4O5S2 385.0640, found 385.0638 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×50 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 over silica gel (70-230 mesh)
  9. washeluted with CH2Cl2:methanol 19:1

Sources & evidence

ORD record
ord-1f269ba9010f43088c3f9f1320cb96d2
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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