Hydrochloric Acid → 3-hydroxy-N-[5-(methylsulfinyl)-1,3-thiazol-2-yl]benzamide

HRID 1620889

Reaction equation

HRID 1620889 reaction equation
Cl.C([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:22])[NH:13][C:14]2[S:15][C:16]([S:19]([CH3:21])=[O:20])=[CH:17][N:18]=2)[CH:7]=1)(=O)C>O1CCCC1>[OH:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:12]([NH:13][C:14]1[S:15][C:16]([S:19]([CH3:21])=[O:20])=[CH:17][N:18]=1)=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 569693943-{[5-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Product 1

HCID 569693963-hydroxy-N-[5-(methylsulfinyl)-1,3-thiazol-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (40.0 mL) is added to a suspension of 8 (0.370 g, 1.13 mmol) in tetrahydrofuran (17.0 mL), and the reaction is warmed to reflux. The reaction becomes homogeneous upon heating. After refluxing for 4 hours, the reaction is allowed to cool to room temperature, and is concentrated in vacuo. The residue is suspended in water and filtered. The filter pad is washed with water, air dried, and then re-dissolved in a minimum amount of warm THF. Water is added to the warm THF solution until the solution turns turbid, and the resulting mixture is allowed to cool to room temperature. Additional water is added, and a white solid forms on standing. The crystalline product is filtered, and the filter pad is washed with water, and dried in vacuo at 70° C. and gives 10 as a white crystalline solid.

Workup

  1. temperaturethe reaction is warmed to reflux
  2. temperatureupon heating
  3. temperatureAfter refluxing for 4 hours
  4. concentrationis concentrated in vacuo
  5. filtrationfiltered
  6. washThe filter pad is washed with water, air
  7. customdried
  8. dissolutionre-dissolved in a minimum amount of warm THF
  9. additionWater is added to the warm THF solution until the solution
  10. temperatureto cool to room temperature
  11. additionAdditional water is added
  12. filtrationThe crystalline product is filtered
  13. washthe filter pad is washed with water
  14. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-1efcfe6a2d384f478d1e037c16ebe4b6
Source dataset
uspto-grants-2014_07
Patent number
US08772502B2

Linked notes

Loading…