HCID 11845249, compound → 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde

HRID 1158871Notes

Reaction equation

HRID 1158871 reaction equation
[N:1]1[N:9]2[C:4]([CH2:5][S:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[CH2:10][OH:11]>O=[Mn]=O.C(Cl)(Cl)Cl>[N:1]1[N:9]2[C:4]([CH2:5][S:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 11845249HCID 11845249, compound

Product 1

HCID 118471336,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

MnO2 (activated) (11.46 g) was added to the CHCl3 (135 mL) solution of (6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)methanol (2.31 g) and refluxed for 1 h under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane—AcOEt (1/1). The titled compound was obtained as pale yellow crystals (1.78 g, 78%).

Workup

  1. temperaturerefluxed for 1 h under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. washthe column was eluted with n-hexane—AcOEt (1/1)

Sources & evidence

ORD record
ord-7ec9bc36c1f54989938c330e611c40b8
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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