Potassium Carbonate → 6-(furan-3-yl)-5-methoxy-2-oxo-2-phenyl-1H-2-lambda*6*-benzo[d][1,2]thiazin-4-one

HRID 2177855Notes

Reaction equation

HRID 2177855 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([O:38][CH3:39])=[C:14]([C:19]([CH2:22][S:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[N:25][C:26](=[O:31])C(F)(F)F)=[O:24])=[CH:20][CH:21]=2)C(OC)=O)=[CH:8]1>CO>[O:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[CH2:22][S:23](=[O:24])([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:25][C:26](=[O:31])[C:14]=3[C:13]=2[O:38][CH3:39])=[CH:8]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86677125methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl)benzoate2×

Product 1

HCID 699150306-(furan-3-yl)-5-methoxy-2-oxo-2-phenyl-1H-2-lambda*6*-benzo[d][1,2]thiazin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.38 g) was added to a stirred solution of methyl 3-(furan-3-yl)-2-methoxy-6-{[S-phenyl-N-(trifluoroacetyl)sulphonimidoyl]methyl)benzoate (Intermediate 215) in methanol (20 ml) and the resultant mixture was stirred at room temperature for 1 hour. The mixture was evaporated to dryness and ethyl acetate and water were added to the residue. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-70%. The isolated product was triturated with diethyl ether and the solid was collected by filtration to give 6-(furan-3-yl)-5-methoxy-2-oxo-2-phenyl-1H-2-λ*6*-benzo[d][1,2]thiazin-4-one (0.23 g) as a white solid.

Workup

  1. customThe mixture was evaporated to dryness and ethyl acetate and water
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-70%
  9. customThe isolated product was triturated with diethyl ether
  10. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-5902efc012d945c19cdb321943b9810b
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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