Hydrochloric Acid → 2H-1-Benzothiopyran-4-carbonitrile

HRID 851164Notes

Reaction equation

HRID 851164 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.C[Si]([C:16]#[N:17])(C)C.O=P(Cl)(Cl)Cl.Cl>C1C=CC=CC=1.[I-].[Zn+2].[I-].ClCCl.N1C=CC=CC=1>[C:16]([C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:1][CH2:2][CH:3]=1)#[N:17]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 19048Thiochroman-4-oneHCID 24813Phosphorus oxychlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 132277052H-1-Benzothiopyran-4-carbonitrile

Reagents, catalysts & solvents 4

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

80 mg of zinc iodide are added to 1.7 g 1-thiochroman-4-one in benzene followed by, dropwise, with stirring at room temperature, 2.4 g of trimethylsilylcyanide. After 8 hours reaction 2.8 ml of POCl3 and 16 ml of pyridine are added and the mixture refluxed for 8 hours. After cooling the mixture is poured onto ice/conc. HCl and, after addition of dichloromethane, separated. The organic phase is dried over MgSO4, concentrated by evaporation and purified by chromatography on kieselgel (eluant hexane/ethyl acetate; 4/1).

Workup

  1. additionare added
  2. temperaturethe mixture refluxed for 8 hours
  3. temperatureAfter cooling the mixture
  4. additionis poured onto ice/conc
  5. customseparated
  6. dry with materialThe organic phase is dried over MgSO4
  7. concentrationconcentrated by evaporation
  8. custompurified by chromatography on kieselgel (eluant hexane/ethyl acetate; 4/1)

Sources & evidence

ORD record
ord-83d457f650f44aeeba63cd10f343b87b
Source dataset
uspto-grants-1983_05
Patent number
US04382951

Reaction notes

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