2-Thiophenecarboxaldehyde, 5-chloro- → HCID 54450680, compound

HRID 596785Notes

Reaction equation

HRID 596785 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH:7]=O)=[CH:5][CH:6]=1.[C:9]([CH:11]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:10]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([CH:7]=[CH:11][C:9]#[N:10])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 85524(Triphenylphosphoranylidene)acetonitrile

Product 1

HCID 54450680HCID 54450680, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-chloro-5-formylthiophene (5.68 g., 40 mM) and cyanomethylenetriphenylphosphorane (12.04 g., 40 mM) in chloroform (100 ml.) was heated under reflux for 20 min., and was evaporated to an oily solid. This was triturated with ether (20 ml.) and colourless needles of triphenylphosphine oxide (m.p. 156°-157°) were filtered off, and were washed with ether (10 ml.). The combined filtrates were evaporated, and the residue was distilled under reduced pressure to give 3-(5-chlorothien-2-yl)acrylonitrile (5.62 g., 83%) as a colourless oil, b.p. 100°-104°/0.6mm., which crystallised in needles, m.p. 41°-43° [Found: C, 49.1; H, 2.5; C1, 21.1; N, 8.3; S, 19.1; C7H4ClNS (169.6) requires C, 49.6; H, 2.4; Cl, 20.9; N, 8.3; S, 18.9%]λmax. 315 nm (ε 21,120).

Workup

  1. temperatureunder reflux for 20 min.
  2. customwas evaporated to an oily solid
  3. customThis was triturated with ether (20 ml.) and colourless needles of triphenylphosphine oxide (m.p. 156°-157°)
  4. filtrationwere filtered off
  5. washwere washed with ether (10 ml.)
  6. customThe combined filtrates were evaporated
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-a8e84d61a6484227a37ae870ae2706e8
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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