Sodium Hydroxide → HCID 66578670, compound

HRID 1521833Notes

Reaction equation

HRID 1521833 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[S:9](=[O:28])(=[O:27])[CH2:10][C:11]3[C:15]([C:16]([O:18]CC)=[O:17])=[N:14][N:13]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:12]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[C:8]2[S:9](=[O:28])(=[O:27])[CH2:10][C:11]3[C:15]([C:16]([OH:18])=[O:17])=[N:14][N:13]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:12]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66581068HCID 66581068, compound

Product 1

HCID 66578670HCID 66578670, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-methoxy-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylate 5,5-dioxide (0.23 g, 0.57 mmol) in THF (10 mL) is added aq. solution of NaOH (2.8 mL, 1 M, 2.85 mmol, 5 Eq) at 0° C. and the reaction mixture is stirred for 4 h. The solvent is removed under reduced pressure and aq. solution of HCl 1 M is added. The product is extracted with EtOAc (2×). The organic layer is washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford 0.2 g (70%) of the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 13.5 (brs, 1H), 7.61-7.57 (m, 3H), 7.46-7.42 (m, 3H), 7.26 (d, J=8.6 Hz, 1H), 6.35 (d, J=8.0 Hz, 1H), 4.88 (s, 2H), 3.90 (s, 3H). MS (ESI+): 371.0. HPLC (max plot) 98.9%; Rt 3.30 min.

Workup

  1. customThe solvent is removed under reduced pressure and aq. solution of HCl 1 M
  2. additionis added
  3. extractionThe product is extracted with EtOAc (2×)
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89ad5d55620f453eb7101bf952ac9b4e
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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