HCID 22758469, compound → HCID 178467280, compound

HRID 1704702Notes

Reaction equation

HRID 1704702 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([N+:17]([O-])=O)[CH:9]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=1)(=[O:4])=[O:3].[H][H].[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28]([OH:35])=[C:29]([C:32](=O)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]>[Pd].C(O)C>[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28](=[O:35])[C:29](=[C:32]([NH:17][C:8]2[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=2)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 22758469HCID 22758469, compoundHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 178467280HCID 178467280, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.5 g. (0.005 mol) of 3,5-bis-methylsulfonamidonitrobenzene in 100 ml. of ethanol and 300 mg. of 10% palladium-on-carbon was hydrogenated in a Parr apparatus until hydrogen uptake had ceased. The catalyst was filtered, the ethanol was removed under reduced pressure and the residue was dissolved in 30 ml. of methanol. This solution of 3,5-bis-methylsulfonamidoaniline (1.36 g.) and 1.06 g. (0.005 mol) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one was refluxed for two hours under nitrogen. The reaction mixture was filtered to give 5-acetyl-4-hydroxy-3-[1-(3,5-bis-methylsulfonamidophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 260° C.

Workup

  1. additionA mixture of 1.5 g
  2. filtrationThe catalyst was filtered
  3. customthe ethanol was removed under reduced pressure
  4. dissolutionthe residue was dissolved in 30 ml
  5. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-e523a4ac4de44a31b2bca91d9aad9fee
Source dataset
uspto-grants-1978_11
Patent number
US04127646

Reaction notes

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