Acetic Acid → HCID 13953802, compound

HRID 1939155Notes

Reaction equation

HRID 1939155 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:15][CH2:14][CH2:13]C(O[Si](C)(C)C)(C#N)[C:11]=2[CH:23]=1.[C:24]([OH:27])(=[O:26])[CH3:25]>C(Cl)(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:15][CH2:14][CH2:13][CH:25]([C:24]([OH:27])=[O:26])[C:11]=2[CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 61436Stannous chloride dihydrateHCID 13014161HCID 13014161, compound

Product 1

HCID 13953802HCID 13953802, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of tin(II) chloride dihydrate (115.42 g, 0.51 mol) and 6-chloro-3,4-dihydro-4-(trimethylsiloxy)-2H-1-benzothiopyran-4-carbonitrile (37.53 g, 0.126 mol) in 1:1 acetic acid/concentrated hydrochloric acid is heated at reflux under nitrogen for 3 days, cooled to room temperature and diluted with chloroform. The aqueous phase is separated and extracted with chloroform. The organic phase and organic extracts are combined and extracted with 2N sodium hydroxide solution. The combined aqueous extracts are washed with chloroform and acidified to pH 3. The acidic aqueous mixture is extracted with chloroform and the combined organic extracts are dried and concentrated in vacuo to obtain a residue. The residue is triturated with an ether/petroleum ether mixture and filtered to give the title product as an off-white solid (12.56 g, mp 139°-150° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 3 days
  3. customThe aqueous phase is separated
  4. extractionextracted with chloroform
  5. extractionextracted with 2N sodium hydroxide solution
  6. washThe combined aqueous extracts are washed with chloroform
  7. extractionThe acidic aqueous mixture is extracted with chloroform
  8. customthe combined organic extracts are dried
  9. concentrationconcentrated in vacuo
  10. customto obtain a residue
  11. customThe residue is triturated with an ether/petroleum ether mixture
  12. filtrationfiltered

Sources & evidence

ORD record
ord-67d9cc2bb0604600a85c000e3f92c544
Source dataset
uspto-grants-1997_12
Patent number
US05696050

Reaction notes

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