Chloroacetonitrile → HCID 21255004, compound

HRID 636421Notes

Reaction equation

HRID 636421 reaction equation
Cl[CH2:2][C:3]#[N:4].[Na+].[C:6]1([CH3:15])[C:7]([S:12]([O-:14])=[O:13])=[CH:8][CH:9]=[CH:10][CH:11]=1>CN(C=O)C>[C:6]1([CH3:15])[C:7]([S:12]([CH2:2][C:3]#[N:4])(=[O:14])=[O:13])=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 23676349Sodium 2-methylbenzene-1-sulfinate

Product 1

HCID 21255004HCID 21255004, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2 ml (34.5 mmol) of chloroacetonitrile were added to a suspension of 4.5 g (28.8 mmol) of toluene-2-sulphinic acid sodium salt in 100 ml of DMF and stirred at 1000 for 1 hr. The reaction solution was evaporated and 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 2.9 g (50%) of (toluene-2-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-f166fbd40ccc4586a66537f44ec79b89
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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