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

HRID 1854285Notes

Reaction equation

HRID 1854285 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:5][N:4]=1.Cl>>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[S:7][C:3]([CH2:2][OH:1])=[N:4][N:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 53321029N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide

Product 1

HCID 533203124-Amino-N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 68.1%

Procedure

Distilled water (3.0 mL) and 10% NaOH (1.5 mL) were added to compound 126 (328 mg, 0.94 mmol) and the mixture was heated under reflux for 2 h. The pH of the solution was then adjusted to 4.0 by addition of 1.0 M HCl and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water (20 mL) and concentrated to give a crude product which was purified by chromatography on silica gel eluted with CH2Cl2:methanol 4:1 to afford 182 mg (0.64 mmol, 68%) of the product as a solid, mp 89-90° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.54 (s, 2H), 5.91 (br, 1H), 6.55 (d, 2H, J=8.7 Hz), 7.39 (d, 2H, J=9.0 Hz); 13C NMR (75 MHz, DMSO-d6) δ 59.1, 113.2, 128.0, 128.4, 153.2, 161.0, 167.5; MS (LCQ, ESI+) Calcd for C9H11N4O3S2 287.0, found 287.0 (M+H)+; HRMS (ESI+, m/z) Calcd for C9H11N4O3S2 287.0273, found 287.0269 (M+H)+.

Workup

  1. distillationDistilled water (3.0 mL) and 10% NaOH (1.5 mL)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 h
  4. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts were washed with water (20 mL)
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by chromatography on silica gel
  9. washeluted with CH2Cl2:methanol 4:1

Sources & evidence

ORD record
ord-9c1c86c249114f7fb91c1b0cd563ec59
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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