HCID 22750628, compound → HCID 22750656, compound

HRID 1439520Notes

Reaction equation

HRID 1439520 reaction equation
[C:1]1([C:7]2[O:8][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:10][C:11](=[O:17])[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1C=CC=CC=1>[C:1]1([C:7]2[O:8][C:9]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:10][C:11](=[O:17])[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 22750628HCID 22750628, compound

Product 1

HCID 22750656HCID 22750656, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 10.0 grams (0.0324 mole) of 5,6-dihydro-2,6-diphenyl-N-methyl-4-oxo-4H-pyran-3-carboxamide, 11.0 grams (0.0485 mole) of dichloro dicyanoquinone and 200 milliliters of benzene is refluxed for 18 hours. The mixture is cooled and the precipitate filtered and washed with benzene and methylenedichloride. The filtrate is evaporated to dryness and the residue is partitioned between methylenedichloride and 2N sodium hydroxide and the layers separated. The organic layer is washed with 2N sodium hydroxide, water and 50 percent brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue is dissolved in a hot 50:50 mixture of ethanol:methanol, treated with decolorizing charcoal, filtered and evaporated in vacuo. The residue is crystallized from ethanol to give 2,6-diphenyl-N-methyl-4-oxo-4H-pyran-3-carboxamide, m.p. 196° C. - 197° C.

Workup

  1. temperatureis refluxed for 18 hours
  2. temperatureThe mixture is cooled
  3. filtrationthe precipitate filtered
  4. washwashed with benzene and methylenedichloride
  5. customThe filtrate is evaporated to dryness
  6. customthe residue is partitioned between methylenedichloride and 2N sodium hydroxide
  7. customthe layers separated
  8. washThe organic layer is washed with 2N sodium hydroxide, water and 50 percent brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. dissolutionThe residue is dissolved in a hot 50:50 mixture of ethanol
  13. additionmethanol, treated with decolorizing charcoal
  14. filtrationfiltered
  15. customevaporated in vacuo
  16. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-374486082cfe4bcba4b35301c3b3c59e
Source dataset
uspto-grants-1977_11
Patent number
US04060533

Reaction notes

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