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

HRID 1620877Notes

Reaction equation

HRID 1620877 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:21])[NH:12][C:13]1[S:14][CH:15]=[C:16]([S:18]([CH3:20])=[O:19])[N:17]=1)(=O)C.Cl>C1COCC1>[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]=[C:16]([S:18]([CH3:20])=[O:19])[N:17]=1)=[O:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 569691682-{[4-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Product 1

HCID 569586142-Hydroxy-N-[4-(methylsulfinyl)-1,3-thiazol-2-yl]benzamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 1 (0.150 g, 0.425 mmol) and THF (11 mL) was added 2M HCl (16 mL). The reaction was warmed to reflux. After refluxing 2 h, the reaction was allowed to cool to room temperature. A solid formed on standing. The reaction was cooled in an ice bath. The cold suspension was filtered. The filter pad was washed with water. The filtrate was concentrated in vacuo. The residue was suspended in water and filtered and combined with the original filter pad. The combined solids were stirred with a mixture of warm methanol and THF, adding more THF until the mixture became homogeneous. The homogeneous solution was concentrated in vacuo. The white residue was suspended in methanol and concentrated in vacuo four more times. The white residue was stirred with ether, filtered and the filter pad dried under a stream of nitrogen to give to give 2 (0.095 g, 79%) as a white solid: mp=240° C. (dec., begins turning dark then melts 260-261° C.). HPLC tR=5.33 min (100%, Condition C). 1H NMR (400 MHz, DMSO-d6) δ 12.18 (br. s., 1H), 11.69 (br. s., 1H), 7.98 (dd, J=2, 8 Hz, 1H), 7.81 (s, 1H), 7.46-7.54 (m, 1H), 6.97-7.10 (m, 2H), 2.86 (s, 3H). MS (ESI+) m/z 305.1 (M+Na)+, 283.1 (M+H)+, MS (ESI−)

Workup

  1. temperatureThe reaction was warmed to reflux
  2. temperatureAfter refluxing 2 h
  3. customA solid formed
  4. temperatureThe reaction was cooled in an ice bath
  5. filtrationThe cold suspension was filtered
  6. washThe filter pad was washed with water
  7. concentrationThe filtrate was concentrated in vacuo
  8. filtrationfiltered
  9. additionadding more THF until the mixture
  10. concentrationThe homogeneous solution was concentrated in vacuo
  11. concentrationconcentrated in vacuo four more times
  12. stirringThe white residue was stirred with ether
  13. filtrationfiltered
  14. customthe filter pad dried under a stream of nitrogen
  15. customto give

Sources & evidence

ORD record
ord-47a2188896ef43fdb8a380f3d8a9aa89
Source dataset
uspto-grants-2014_07
Patent number
US08772502B2

Reaction notes

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