Potassium Carbonate → (2,3-Dihydro-1,4-benzoxathiin-2-yl)acetonitrile

HRID 1391067Notes

Reaction equation

HRID 1391067 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH:10]([CH2:14]Br)[CH2:11][C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:14][CH:10]1[CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 118311393,4-Dibromobutanenitrile

Product 1

HCID 20540157(2,3-Dihydro-1,4-benzoxathiin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The starting material is prepared as follows: To the stirred, refluxing solution of 21 g of 2-hydroxy-thiophenol in 290 ml of acetone is added dropwise 12.5 g of 3,4-dibromo-butyronitrile along with small portions of 15.8 g of anhydrous potassium carbonate. After 30 minutes, the double addition procedure with said amounts of dibromo compound and potassium carbonate is repeated, and after a further 30 minutes said procedure is repeated a third time. The mixture is then refluxed for 20 hours, cooled, filtered, and the residual salts washed with acetone, and the filtrate evaporated. The residue is distilled (bulb to bulb), and the fraction boiling at 185°/0.5 mm Hg collected, to yield the 2-(1,4-benzoxathian-2-yl)-acetonitrile.

Workup

  1. customThe starting material is prepared
  2. additionthe double addition procedure
  3. waitafter a further 30 minutes said
  4. temperatureThe mixture is then refluxed for 20 hours
  5. temperaturecooled
  6. filtrationfiltered
  7. washthe residual salts washed with acetone
  8. customthe filtrate evaporated
  9. distillationThe residue is distilled (bulb to bulb)
  10. customthe fraction boiling at 185°/0.5 mm Hg collected

Sources & evidence

ORD record
ord-68c7a4a8edeb4cc7b96dd4cf17e83f02
Source dataset
uspto-grants-1979_02
Patent number
US04140781

Reaction notes

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