Chloroacetonitrile → HCID 21823271, compound

HRID 636423Notes

Reaction equation

HRID 636423 reaction equation
Cl[CH2:2][C:3]#[N:4].[Na+].[C:6]1([CH3:15])[CH:11]=[CH:10][CH:9]=[C:8]([S:12]([O-:14])=[O:13])[CH:7]=1>CN(C=O)C>[C:6]1([CH3:15])[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 23703014Sodium 3-methylbenzene-1-sulfinate

Product 1

HCID 21823271HCID 21823271, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.65 ml (42 mmol) of chloroacetonitrile were added to a suspension of 7.5 g (42 mmol) of toluene-3-sulphinic acid sodium salt in 80 ml of DMF and stirred at 100° 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, CH2Cl2) yielded 2.06 g (25%) of (toluene-3-sulphonyl)-acetonitrile as a colorless oil.

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-3c2d35598e2b4f1d88e1d600ef85c5df
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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