Chloroacetonitrile → Phenylsulphonylacetonitrile

HRID 435726Notes

Reaction equation

HRID 435726 reaction equation
[Na+].[C:2]1([S:8]([O-:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:12][C:13]#[N:14]>CN(C)C=O>[C:2]1([S:8]([CH2:12][C:13]#[N:14])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 82077Phenylsulphonylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Benzene sulfinic acid sodium salt, 49.2 g. (0.3 mole) was combined with 400 ml. of dimethyl formamide in a 1 liter flask. The mixture was stirred at 40° C. Chloroacetonitrile, 22.5 g. (0.3 mole) was added over a period of 5 minutes. The resulting mixture was stirred and heated at 40°-45° C. for 2 hours. The reaction mass was then poured into 600 ml. of water, and the solid insoluble product was collected by suction filtration and dried. There was obtained a yield of 29.8 g. of the title compound, m.p. 111°-112° C.

Workup

  1. addition(0.3 mole) was added over a period of 5 minutes
  2. stirringThe resulting mixture was stirred
  3. temperatureheated at 40°-45° C. for 2 hours
  4. additionThe reaction mass was then poured into 600 ml
  5. filtrationof water, and the solid insoluble product was collected by suction filtration
  6. customdried
  7. customThere was obtained a yield of 29.8 g

Sources & evidence

ORD record
ord-397ffe70982344d1a2d06cd90095ce97
Source dataset
uspto-grants-1977_02
Patent number
US04006154

Reaction notes

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