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

HRID 1620883Notes

Reaction equation

HRID 1620883 reaction equation
Cl.C([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[NH:13][C:14]2[S:15][CH:16]=[C:17]([S:19]([CH3:21])=[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]([CH3:21])=[O:20])[N:18]=2)=[O:22])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 569693894-{[4-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Product 1

HCID 569693904-hydroxy-N-[4-(methylsulfinyl)-1,3-thiazol-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (3.0 mL) is added to a suspension of 3 (0.12 g, 0.33 mmol) in tetrahydrofuran (3.0 mL), and the resulting suspension is warmed to reflux. The reaction becomes homogeneous upon heating. After refluxing for 1.5 h, the reaction is allowed to cool to room temperature, and is then partitioned between diethyl ether and water. The ether layer is washed with water, saturated aqueous sodium bicarbonate, and brine. The ether layer is dried with anhydrous sodium sulfate and concentrated in vacuo. The residue is triturated with ethyl acetate, the solvent is removed under a stream of nitrogen, and the resulting solid is dried in vacuo at 55° C. to give 4 as a light yellow solid.

Workup

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

Sources & evidence

ORD record
ord-fc19431417ff415fac5580dbeab6cd1f
Source dataset
uspto-grants-2014_07
Patent number
US08772502B2

Reaction notes

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