Hydrochloric Acid → 1-(3-Thienyl)cyclopropanecarbonitrile

HRID 2393460Notes

Reaction equation

HRID 2393460 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#[N:8])=[CH:2]1.Br[CH2:10][CH2:11]Cl.[H-].[Na+].Cl>CS(C)=O.O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2([C:7]#[N:8])[CH2:11][CH2:10]2)=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 837303-Thienylacetonitrile

Product 1

HCID 189757181-(3-Thienyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of thiophene-3-acetonitrile (30 g) and 1-bromo-2-chloroethane (40.8 ml) in dimethyl sulphoxide (120 ml) was added slowly dropwise to a well stirred suspension of sodium hydride (60% dispersion in mineral oil; 38.8 g) in dimethyl sulphoxide (800 ml) at 30°-35° C. The solution was stirred at ambient temperature for 21 hours then water (100 ml) was carefully added followed by hydrochloric acid (2M; 100 ml). The mixture was extracted with ether (6×80 ml) and the combined extracts washed with water (2×100 ml) then brine and then dried over magnesium sulphate. The solvent was removed in vacuo and the residue washed with petroleum ether (bp 60°-80° C.) before distillation under reduced pressure which gave 1-(3-thienyl)cyclopropanecarbonitrile as an oil (26.3 g), bp 82°-86° C./2 mbar.

Workup

  1. stirringThe solution was stirred at ambient temperature for 21 hours
  2. extractionThe mixture was extracted with ether (6×80 ml)
  3. washthe combined extracts washed with water (2×100 ml)
  4. dry with materialbrine and then dried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. washthe residue washed with petroleum ether (bp 60°-80° C.) before distillation under reduced pressure which

Sources & evidence

ORD record
ord-dc291176d2624ddabe556002049362fe
Source dataset
uspto-grants-1998_09
Patent number
US05807868

Reaction notes

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