Pyridine → HCID 86743768, compound

HRID 1199887Notes

Reaction equation

HRID 1199887 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][S:3]1.Cl.[NH2:15][OH:16].N1C=CC=CC=1>C(O)C>[CH3:1][C:2]1([CH3:13])[C:11](=[N:15][OH:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][S:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 19864115HCID 19864115, compound

Product 1

HCID 86743768HCID 86743768, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.0 g of 3,3-dimethylisothiochroman-4-one, 8.0 g of hydroxylamine hydrochloride, 18 ml of pyridine and 60 ml of ethanol is heated at reflux for 60 hours. The cooled reaction mixture is concentrated by evaporation, then toluene is added and the mixture is again concentrated by evaporation. The residue is boiled up in dichloromethane, cooled and filtered. The filtrate is concentrated by evaporation and the residue is chromatographed with silica gel (eluant: ethyl acetate/hexane 1:12). Concentration of the eluate by evaporation yields 6.0 g of 3,3-dimethylisothiochroman-4-oneoxime in the form of yellow crystals having a melting point of 83°-84° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 60 hours
  3. customThe cooled reaction mixture
  4. concentrationis concentrated by evaporation
  5. additiontoluene is added
  6. concentrationthe mixture is again concentrated by evaporation
  7. temperaturecooled
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated by evaporation
  10. customthe residue is chromatographed with silica gel (eluant: ethyl acetate/hexane 1:12)
  11. customConcentration of the eluate by evaporation

Sources & evidence

ORD record
ord-bc4318e953e14c9db6da26047b283b81
Source dataset
uspto-grants-1990_02
Patent number
US04904300

Reaction notes

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