Phosphorus oxychloride → 3-(2-Thienyl)-2-propenenitrile

HRID 596772Notes

Reaction equation

HRID 596772 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH2:10])=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].P(Cl)(Cl)(Cl)=O>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]#[N:10]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 912113-(2-Thienyl)acrylamideHCID 656671Sodium Pyrosulfite

Product 1

HCID 1111403-(2-Thienyl)-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

β-(Thien-2-yl) acrylamide (5.2 g.) was mixed with sodium metabisulphite (12.9 g.) and heated with phosphoryl chloride (2.4 ml.) on a steam bath. After 1 hr., more phosphoryl chloride (10 ml.) was added and the mixture heated for a further 3.5 hrs. The mixture was cooled in an ice-bath and iced water cautiously added. The mixture was extracted into chloroform and the chloroform layer was washed with saturated sodium hydrogen carbonate solution, dried over sodium sulphate, and evaporated in vacuo to a brown oil. Distillation gave β-(thien-2 -yl) acrylonitrile, 1.50 g. (33%), b.p. 82- 86° /0.5 mm., λmax. (EtOH) 306 nm, (ε 18600).

Workup

  1. temperaturethe mixture heated for a further 3.5 hrs
  2. temperatureThe mixture was cooled in an ice-bath
  3. extractionThe mixture was extracted into chloroform
  4. washthe chloroform layer was washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo to a brown oil
  7. distillationDistillation

Sources & evidence

ORD record
ord-279fc58f864a40f0ace06c9667e3d612
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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