Hydrochloric Acid → 2-(5-(4-Aminophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic Acid

HRID 631059

Reaction equation

HRID 631059 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[S:19][C:18]([CH2:20][C:21]([O:23]CC)=[O:22])=[N:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.Cl>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[S:19][C:18]([CH2:20][C:21]([OH:23])=[O:22])=[N:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 53323731Ethyl 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate

Product 1

HCID 533263022-(5-(4-Aminophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic AcidYield 82.1%

Procedure

Distilled water (3.0 mL) and 10% aqueous NaOH (1.5 mL) were added to compound 118E (300 mg, 0.78 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, the resulting precipitate was isolated by filtration, washed with cold water, and dried to give 201 mg (0.64 mmol, 82%) of the product as a solid, mp 209-210° C.; 1H NMR (600 MHz, DMSO-d6) δ 3.59 (s, 2H), 6.52 (d, 2H, J=8.1 Hz), 7.42 (d, 2H, J=8.9 Hz); 13C NMR (75 MHz, DMSO-d6) δ 36.6, 113.3, 127.8, 128.4, 152.4, 153.3, 167.7, 170.4; MS (LCQ, ESI+) Calcd for C10H11N4O4S2 315.0. found 315.0 (M+H)+. HRMS (ESI+, m/z) Calcd for C10H11N4O4S2 315.0222. found 315.0220 (M+H)+.

Workup

  1. distillationDistilled water (3.0 mL) and 10% aqueous NaOH (1.5 mL)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 h
  4. customthe resulting precipitate was isolated by filtration
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-4c853679094e4a679018095f7d964f24
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Linked notes

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