Lithium cyanide → HCID 19982141, compound

HRID 1460505Notes

Reaction equation

HRID 1460505 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH:8]([CH2:11][C:12](O)=O)[CH2:7][C:6]=2[CH:15]=1.F[C:17]1[CH:18]=[CH:19][C:20]2SCC(CI)CC=2[CH:28]=1.[C-]#[N:30].[Li+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH:8]([CH2:11][CH2:12][N:30]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:28]3)[CH2:7][C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 75478Lithium cyanideHCID 19982154HCID 19982154, compoundHCID 19982163HCID 19982163, compound

Product 1

HCID 19982141HCID 19982141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material is prepared as follows: 6-Fluoro-3,4-dihydro-2H-1-benzothiopyran-3-ylacetic acid: A mixture of 3.8 g 6-fluoro-3-iodomethyl-3,4-dihydro-2H-1-benzothiopyran and 30 ml 0.5 M lithium cyanide in dimethylformamide is stirred at room temperature for 24 hours after which it is poured onto water. The product is extracted with ether. After drying over magnesium sulfate the solvent is removed in vacuo. This residue is refluxed in a mixture of 20 ml acetic acid and 20 ml 12 N HCl for 6 hours. The solvent is removed in vacuo, the residue is dissolved in 1 N NaOH and washed with ether. The aqueous phase is acidified with 3 N HCl and the product is extracted with ether. After drying over magnesium sulfate, the solvent is removed in vacuo. The residue is triturated with ether/hexane and affords the title compound, m.p. 125°-135° C.

Workup

  1. customThe starting material is prepared
  2. additionis poured onto water
  3. extractionThe product is extracted with ether
  4. dry with materialAfter drying over magnesium sulfate the solvent
  5. customis removed in vacuo
  6. temperatureThis residue is refluxed in a mixture of 20 ml acetic acid and 20 ml 12 N HCl for 6 hours
  7. customThe solvent is removed in vacuo
  8. dissolutionthe residue is dissolved in 1 N NaOH
  9. washwashed with ether
  10. extractionthe product is extracted with ether
  11. dry with materialAfter drying over magnesium sulfate
  12. customthe solvent is removed in vacuo
  13. customThe residue is triturated with ether/hexane

Sources & evidence

ORD record
ord-40c2335ba801451facf2944ada010a17
Source dataset
uspto-grants-1991_12
Patent number
US05071858

Reaction notes

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