Chloroacetonitrile → (Pyridine-3-sulphonyl)-acetonitrile

HRID 636425Notes

Reaction equation

HRID 636425 reaction equation
Cl[CH2:2][C:3]#[N:4].[Na+].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12]([O-:14])=[O:13])[CH:7]=1>CN(C=O)C>[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12]([CH2:2][C:3]#[N:4])(=[O:14])=[O:13])[CH:7]=1

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 23697071Sodium pyridine-3-sulfinate

Product 1

HCID 21254898(Pyridine-3-sulphonyl)-acetonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 ml (33.4 mmol) of chloroacetonitrile were added to a solution of 4.6 g (42 mmol) of pyridine-3-sulphinic acid sodium salt in 50 ml of DMF and stirred at 90° for 1 hr. The reaction solution was evaporated, the residue was partitioned between H2O and CH2Cl2. The aqueous phase was washed three times with CH2Cl2. The combined organic phases were washed once with H2O, dried (MgSO4) filtered and evaporated. Chromatography (SiO2, AcOEt/hexane 2:1) yielded 4.1 g (80%) of (pyridine-3-sulphonyl)-acetonitrile as a beige solid.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between H2O and CH2Cl2
  3. washThe aqueous phase was washed three times with CH2Cl2
  4. washThe combined organic phases were washed once with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-71acbc7dcf784c80b3ea50e3335f3874
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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