Acetonitrile → HCID 18921799, compound

HRID 1289491Notes

Reaction equation

HRID 1289491 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7]Cl)=[CH:2]1.[C:9](#[N:11])[CH3:10].[Sn](Cl)(Cl)(Cl)Cl>O>[CH3:10][CH:9]1[C:2]2[S:1][CH:5]=[CH:4][C:3]=2[CH:6]=[CH:7][NH:11]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24287Tin tetrachlorideHCID 14548174HCID 14548174, compound

Product 1

HCID 18921799HCID 18921799, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(3-thienyl)chloroethane(20 g, 0.136 mol) prepared in the above Step 1 and anhydrous acetonitrile(350 ml) was added tin(IV) chloride(20 ml, 0.17 mol) at room temperature. The reaction mixture was heated to reflux for 16 hours and cooled, to which water was added to remove excess tin(IV) chloride. And then the reaction mixture was washed by dichloromethane. The water layer was separated and basified with aqueous K2CO3 solution under ice-cooling and then extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate and concentrated to give 10.56 g of the titled compound. (Yield: 51%)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. additionwas added
  4. customto remove excess tin(IV) chloride
  5. washAnd then the reaction mixture was washed by dichloromethane
  6. customThe water layer was separated
  7. temperaturecooling
  8. extractionextracted with dichloromethane
  9. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-85349ecb0fba4f7fa02ec080a035f84e
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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