Hydroxyacetonitrile → Cyanomethyl thiophene-2-sulfonate
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
Product 1
Reagents, catalysts & solvents 1
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
- customMethod of preparation
- customas described in the previous example, with 2 hours of reaction at 0° C.
- customthe bottom dark layer is isolated
- washthe solution washed with weak caustic solution and cold water
- 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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