HCID 9971204, compound → HCID 12208315, compound

HRID 865946Notes

Reaction equation

HRID 865946 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].S1[C:18]2[N+:9](=[CH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH:17]=2)C=C1.O1C=CC(C(C2C=COC=2)=C)=C1>[N+](C)([O-])=O>[Cl:1]([OH:5])(=[O:4])(=[O:3])=[O:2].[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][N:9]=1

Participants

4

Reactant 2

HCID 9971204HCID 9971204, compoundHCID 10464590HCID 10464590, compound

Product 1

HCID 12208315HCID 12208315, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of 1.5 g (0.01 mol)) of thiazolo[3,2-b]isoquinolinium perchlorate and 1.3 g (8 mmol) of 1,1-di-(3-furyl)ethylene in 50 ml of nitromethane was heated to reflux under nitrogen for 3 h. The mixture was cooled and concentrated in vacuo. The residue was triturated with ether/ethyl acetate (75 ml), filtered to yield a crude product. This solid was triturated in 50 ml of methylene chloride and the solid was collected by filtration. The solid product was washed with ether, isopropanol, methylene chloride, and dried to afford 1.7 g of 11,11-di(3-furyl)-5,10-ethano-5,10-dihydrothiazolo-3,2-b]isoquinolin perchlorate (Formula I: A=thiazolo;R1 =R2 =R3 =R6 =H; R4 =R5 =3-furanyl;X- =ClO4-).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 3 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether/ethyl acetate (75 ml)
  6. filtrationfiltered
  7. customto yield a crude product
  8. customThis solid was triturated in 50 ml of methylene chloride
  9. filtrationthe solid was collected by filtration
  10. washThe solid product was washed with ether, isopropanol, methylene chloride
  11. customdried

Sources & evidence

ORD record
ord-311e10c7b00a42a185f2e5dca1bd4ea5
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

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