Hydrochloric Acid → Benzamide, 2-hydroxy-N-2-thiazolyl-

HRID 341264Notes

Reaction equation

HRID 341264 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:18])[NH:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)(=O)C.Cl>>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:18]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 3363745Nitazoxanide Impurity

Product 1

HCID 578639Benzamide, 2-hydroxy-N-2-thiazolyl-Yield 86.4%

Conditions

Temperature
50 °C

Procedure

2-(1,3-thiazol-2-ylcarbamoyl)phenyl acetate (501, 663.3 mg, 2.53 mmol) was added to a 25 mL round bottom flask equipped with a stirbar and a water-jacketed condenser. The headspace was replaced with dry nitrogen, and concentrated hydrochloric acid (15.0 mL) was added in a single portion. The suspension was heated to 50° C., and stirred well. The suspended solids dissolved to form a clear colorless solution before solids precipitate from the reaction mixture, which was then cooled in an ice bath, and the solids were filtered on a medium frit and washed with a large portion of water. The filter cake wash washed through the frit with methanol, collected, and the solvent was removed in vacuo to give 502 (481.5 mg, 86%) as a colorless solid.

Workup

  1. customequipped with a stirbar and a water-jacketed condenser
  2. additionwas added in a single portion
  3. dissolutionThe suspended solids dissolved
  4. customto form a clear colorless solution before solids
  5. customprecipitate from the reaction mixture, which
  6. temperaturewas then cooled in an ice bath
  7. filtrationthe solids were filtered on a medium frit
  8. washwashed with a large portion of water
  9. washThe filter cake wash
  10. washwashed through the frit with methanol
  11. customcollected
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4f23de429ac14c3b9460f7c75ae2880a
Source dataset
uspto-grants-2014_11
Patent number
US08895752B2

Reaction notes

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