Chloroacetonitrile → [(3,4-Dichlorophenyl)sulfanyl]acetonitrile

HRID 2413332

Reaction equation

HRID 2413332 reaction equation
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[CH:7]=[C:8]([S:13][Si](C)(C)C)[CH:9]=[CH:10][C:11]=1[Cl:12]>C(#N)C.CN(C)P(=O)(N(C)C)N(C)C>[Cl:5][C:6]1[CH:7]=[C:8]([S:13][CH2:2][C:3]#[N:4])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 20491069[(3,4-Dichlorophenyl)sulfanyl](trimethyl)silane

Product 1

HCID 18542995[(3,4-Dichlorophenyl)sulfanyl]acetonitrileYield 96.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

3.5 ml (55 mmoles) of chloroacetonitrile were added to a refluxing solution of 11.0 g (44 mmoles) of 3,4-dichlorophenylthio(trimethyl)silane in a mixture of 25 ml of acetonitrile and 10 ml of hexamethylphosphoric triamide and the reaction was complete with 2 minutes. The residue obtained after evaporation of the acetonitrile was dissolved in ethyl acetate, and the solution was washed with water, dried and evaporated to dryness to obtain 9.30 g (93% yield) of (3,4-dichlorophenylthio)acetonitrile boiling at 127°-130° C./0.4 mm Hg and having a refractive index of nD25 =1.5920.

Workup

  1. customThe residue obtained
  2. customafter evaporation of the acetonitrile
  3. dissolutionwas dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-16346bd1c6314838abc2eabb84ef2837
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Linked notes

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