Potassium Iodide → 2-(Thiochroman-8-yl-oxy)acetonitrile

HRID 274749Notes

Reaction equation

HRID 274749 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:21][C:22]#[N:23]>CN(C)C=O>[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:21][C:22]#[N:23])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 1216173,4-dihydro-2H-1-benzothiopyran-8-ol

Product 1

HCID 200936122-(Thiochroman-8-yl-oxy)acetonitrileYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under argon, 2 g (12.03 mmol) of 8-thiochromanol are dissolved in 15 cm3 of DMF. 5 g (36.09 mmol) of potassium carbonate and a catalytic amount of potassium iodide are added. Then 5.45 g (72.18 mmol) of chloroacetonitrile dissolved in 5 cm3 of dimethylformamide (DMF) are added dropwise. The mixture is heated at 60° C. for 4 hours, and then the solvent is evaporated off. The residue is taken up in H2O and extracted with methylene chloride and then dried over MgSO4. After evaporation, the product is purified over a silica column. Eluant: methanol/CH2Cl2 1:99. 2.44 g of 2-(thiochroman-8-yl-oxy)acetonitrile are obtained (melting point: 66° C.).

Workup

  1. additionare added dropwise
  2. customthe solvent is evaporated off
  3. extractionextracted with methylene chloride
  4. dry with materialdried over MgSO4
  5. customAfter evaporation
  6. customthe product is purified over a silica column

Sources & evidence

ORD record
ord-735cb632e0ed4de4abb7690aafb52fd3
Source dataset
uspto-grants-1995_02
Patent number
US05389668

Reaction notes

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