Hydrochloric Acid → HCID 19037054, compound

HRID 264847Notes

Reaction equation

HRID 264847 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[CH2:10][C:9](=O)[C:8]=2[CH:19]=1)([O-:3])=[O:2].C[Si]([C:24]#[N:25])(C)C.P(Cl)(Cl)(Cl)=O.Cl>[I-].[Zn+2].[I-].N1C=CC=CC=1.C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[CH:10]=[C:9]([C:24]#[N:25])[C:8]=2[CH:19]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 82115Trimethylsilyl cyanideHCID 19037068HCID 19037068, compound

Product 1

HCID 19037054HCID 19037054, compound

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

To a mixture of 3.08 g of 3,4-dihydro-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-one and 40 ml of dried benzene was added 1.8 ml of trimethylsilyl cyanide with stirring under ice-cooling. 1.22 g of zinc iodide was added therein and the resultant mixture was stirred at room temperature for 19 hours. 6 ml of pyridine and 3.1 ml of phosphorus oxychloride were added therein and the mixture was refluxed with heating for 5.5 hours. Ice water was added to the residue, and the residue was acidified to be hydrochloric acid and extracted with methylene chloride. An organic layer was washed with water and dried, and the solvent was distilled. The resultant residue was purified according to silica gel column chromatography (developing solution: CH2Cl2) to obtain 0.28 g of 6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-carbonitrile with a melting point of 175°-176° C.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 5.5 hours
  4. extractionextracted with methylene chloride
  5. washAn organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled
  8. customThe resultant residue was purified

Sources & evidence

ORD record
ord-6921e48d137d48698d70c7adaa649db0
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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