Acetic Acid → HCID 52950390, compound

HRID 1521858Notes

Reaction equation

HRID 1521858 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=3[S:13][CH2:14][C:5]=2[C:4]([C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])=[N:3]1.OO.[OH2:28].C(O)(=[O:31])C>>[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=3[S:13](=[O:31])(=[O:28])[CH2:14][C:5]=2[C:4]([C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])=[N:3]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 66579017HCID 66579017, compound

Product 1

HCID 52950390HCID 52950390, compound

Procedure

A solution of 1-methyl-3-(morpholin-4-ylcarbonyl)-8-nitro-1,4-dihydrothiochromeno[4,3-c]pyrazole (0.084 g, 0.23 mmol) in acetic acid is heated at 100° C. under nitrogen. Hydrogen peroxide 30% in water (0.5 mL, 3.6 mmol, 15 Eq) is added and the reaction mixture is heated for 30 minutes. After 30 minutes, the solvent is removed under reduced pressure. 10% aqueous NaHCO3 is added to the residue. The mixture is stirred for few minutes and then extracted with DCM. The organic layer is concentrated and purified by column chromatography to afford the title compound as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.66 (s, 1H), 8.48 (dd, J=8.5 Hz, J=2.3 Hz, 1H), 8.28 (J=11.8 Hz, 1H), 4.96 (s, 2H), 4.33 (s, 3H), 3.94 (brs, 2H), 3.66-3.63 (m, 6H). MS (ESI+): 393.0. HPLC (max plot) 90.8%; Rt 3.08 min.

Workup

  1. temperaturethe reaction mixture is heated for 30 minutes
  2. customthe solvent is removed under reduced pressure
  3. addition10% aqueous NaHCO3 is added to the residue
  4. extractionextracted with DCM
  5. concentrationThe organic layer is concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-c660533a603c409e8ff8ac5cfcf9182b
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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