Water → HCID 9859623, compound

HRID 1825724Notes

Reaction equation

HRID 1825724 reaction equation
C[O-].[Na+].[S:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:14])[CH2:5]1.[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.O>CN(C)C=O>[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1/[CH:20]=[C:5]1\[S:4][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]\1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 13854Pyrrole-2-carboxaldehydeHCID 213964H-1,4-Benzothiazin-3-oneHCID 10942334Sodium Methoxide

Product 1

HCID 9859623HCID 9859623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium methoxide (0.28 g, 5.2 mmol) was added to a solution of 2H-1,4-benzothiazin-3(4H)-one (0.60 g, 4 mmol) and pyrrol-2-carboxaldehyde (0.49 g, 5.2 mmol) in dry N,N-dimethylformamide (3.5 ml) (hereinafter “DMF”). The mixture was heated at 120° C. for 6.5 h, allowed to cool and poured into water (60 ml). The precipitate was collected by filtration and washed with water. The precipitate was dissolved in ethyl acetate and the insoluble black residue was filtered out. The filtrate was concentrated, then chromatographed on a silica column using a gradient of 100% dichloromethane to (100:1) dichloromethane:ethanol as the mobile phase. The first eluted product was the (E)-isomer.

Workup

  1. temperatureto cool
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dissolutionThe precipitate was dissolved in ethyl acetate
  5. filtrationthe insoluble black residue was filtered out
  6. concentrationThe filtrate was concentrated
  7. customchromatographed on a silica column

Sources & evidence

ORD record
ord-3346707bb3e24281ae5e5faf76f49391
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

Loading…