4H-1,4-Benzothiazin-3-one → 2-[(4,5-Dimethylpyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one

HRID 1825726Notes

Reaction equation

HRID 1825726 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[NH:5][C:6]=1[CH3:7].[S:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12](=[O:20])[CH2:11]1.C[O-].[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:11]2[C:12](=[O:20])[NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:10]2)[NH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 213964H-1,4-Benzothiazin-3-oneHCID 5789704,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 696371552-[(4,5-Dimethylpyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4,5-Dimethylpyrrole-2-carboxaldehyde (0.27 g, 2.19 mmol) was added to a solution of 2H-1,4-benzothiazin-3(4H)-one (0.36 g, 2.19 mmol) and sodium methoxide (0.118 g, 2.19 mmol) in dry DMF (2 ml). The mixture was heated at 120° C. for 48 h, allowed to cool and poured into ice-water (50 ml). The precipitated solid was collected by filtration, washed with water, then dissolved in ethanol. The insoluble black residue was filtered out and the filtrate was concentrated to dryness under reduced pressure. The product was purified by silica gel chromatography using (98:2) dichloromethane:methanol as the mobile phase.

Workup

  1. temperatureto cool
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in ethanol
  5. filtrationThe insoluble black residue was filtered out
  6. concentrationthe filtrate was concentrated to dryness under reduced pressure
  7. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e46acb143ce048a68414bf110b959352
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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