Hydroxyacetonitrile → Cyanomethyl thiophene-2-sulfonate

HRID 437178Notes

Reaction equation

HRID 437178 reaction equation
[C:1](#[N:4])[CH2:2][OH:3].[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[S:10](Cl)(=[O:12])=[O:11]>C(OCC)C>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[S:10]([O:3][CH2:2][C:1]#[N:4])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 7857HydroxyacetonitrileHCID 855182-Thiophenesulfonyl chloride

Product 1

HCID 20556342Cyanomethyl thiophene-2-sulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Method of preparation: Glycolonitrile is reacted with 2-thiophenesulfonyl chloride using the procedure as described in the previous example, with 2 hours of reaction at 0° C., followed by three hours at room temperature. The reaction mixture separates into two layers; the bottom dark layer is isolated and dissolved in diethyl ether, the solution washed with weak caustic solution and cold water, and the solvent is stripped off under reduced pressure to give the product (in 79% conversion), a green oily liquid, nD24.5 1.535.

Workup

  1. customMethod of preparation
  2. customas described in the previous example, with 2 hours of reaction at 0° C.
  3. customthe bottom dark layer is isolated
  4. washthe solution washed with weak caustic solution and cold water
  5. customto give the product (in 79% conversion)

Sources & evidence

ORD record
ord-022c477181ea4de59e8ceadaf7dfd2ed
Source dataset
uspto-grants-1977_06
Patent number
US04029809

Reaction notes

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