(Triphenylphosphoranylidene)acetonitrile → 3-(5-Methylthiothien-2-yl)-acrylonitrile

HRID 596787Notes

Reaction equation

HRID 596787 reaction equation
[CH:1]([C:3]1[S:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=1)=O.[C:10]([CH:12]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:11]>C(Cl)(Cl)Cl>[CH3:9][S:8][C:5]1[S:4][C:3]([CH:1]=[CH:12][C:10]#[N:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 27369975-(Methylsulfanyl)thiophene-2-carbaldehyde

Product 1

HCID 540859163-(5-Methylthiothien-2-yl)-acrylonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-formyl-5-methylthiothiphene (9.11 g., 58 mmole) and cyanomethylenetriphenylphosphorane (19.1 g., 64 mmole) in chloroform (200 ml.) was stirred at room temperature for 1 hr., and was then heated under reflux for 10 mins. to complete the reaction. The solvent was removed, and the residue was triturated with dry ether (50 ml.). Colourless crystals of triphenylphosphine oxide (m.p. 156°-157°), were filtered off, and were washed with ether (10 ml.). The combined filtrates were evaporated, and the dark red oily residue was distilled under reduced pressure to give 3-(5-methylthiothien-2-yl)-acrylonitrile (8.33 g., 80%) as a pale-yellow oil, b.p. 124°-135°/0.7 mm., λmax. 350, 241 nm, (ε 3440, 1460) [Found (on a redistilled sample): C, 52.9; H, 3.8; N, 7.4; S, 35.7. C8H7NS2 (181.3) requires C, 53.0; H, 3.9; N, 7.7; S, 35.4%].

Workup

  1. temperature, and was then heated
  2. temperatureunder reflux for 10 mins
  3. customthe reaction
  4. customThe solvent was removed
  5. customthe residue was triturated with dry ether (50 ml.)
  6. filtrationColourless crystals of triphenylphosphine oxide (m.p. 156°-157°), were filtered off
  7. washwere washed with ether (10 ml.)
  8. customThe combined filtrates were evaporated
  9. distillationthe dark red oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5c67314c5e4c4d0f947d58853382ba76
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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