Hydrochloric Acid → 4-hydroxy-N-[4-(methylsulfonyl)-1,3-thiazol-2-yl]benzamide

HRID 1644766Notes

Reaction equation

HRID 1644766 reaction equation
Cl.C([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:23])[NH:13][C:14]2[S:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[N:18]=2)=[CH:8][CH:7]=1)(=O)C>O1CCCC1>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:13][C:14]2[S:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[N:18]=2)=[O:23])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 251869354-{[4-(Methylsulfonyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Product 1

HCID 509050604-hydroxy-N-[4-(methylsulfonyl)-1,3-thiazol-2-yl]benzamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (3.0 mL) was added to a suspension of 83 (0.12 g, 0.35 mmol) in tetrahydrofuran (3.0 mL), and the resulting suspension was warmed to reflux. The reaction became homogeneous upon heating. After refluxing for 1.5 h, the reaction was allowed to cool to room temperature, and then partitioned between diethyl ether and water. The ether layer was washed with water, saturated aqueous sodium bicarbonate, and brine. The ether layer was dried with anhydrous sodium sulfate and concentrated in vacuo. The residue triturated with ethyl acetate, the solvent was removed under a stream of nitrogen, and the resulting solid was dried in vacuo at 55° C. to give 84 (0.086 g, 82%) as a light yellow solid.

Workup

  1. temperaturethe resulting suspension was warmed to reflux
  2. temperatureupon heating
  3. temperatureAfter refluxing for 1.5 h
  4. custompartitioned between diethyl ether and water
  5. washThe ether layer was washed with water, saturated aqueous sodium bicarbonate, and brine
  6. dry with materialThe ether layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue triturated with ethyl acetate
  9. customthe solvent was removed under a stream of nitrogen
  10. customthe resulting solid was dried in vacuo at 55° C.

Sources & evidence

ORD record
ord-2942c9a9dc6f414a9b53fb1842c84ce9
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Reaction notes

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