Chloroacetonitrile → HCID 19099264, compound

HRID 1975473Notes

Reaction equation

HRID 1975473 reaction equation
[S:1]1[C:5]([S-:6])=[CH:4][N:3]=[N:2]1.[Na+].Cl[CH2:9][C:10]#[N:11]>ClCCl.CN(C)C=O>[S:1]1[C:5]([S:6][CH2:9][C:10]#[N:11])=[CH:4][N:3]=[N:2]1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 109315095-Mercapto-1,2,3-thiadiazole sodium salt

Product 1

HCID 19099264HCID 19099264, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of sodium 1,2,3-thiadiazol-5-thiolate (15 g) in dichloromethane (150 ml) and dimethylformamide (20 ml) was added chloroacetonitrile (4.76 ml) at room temperature. After stirring overnight, the precipitate was filtered off and the filtrate was poured into the mixture of water (30 ml) and dichloromethane (300 ml). The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (450 ml) eluting with ethyl acetate to give (1,2,3-thiadiazol-5-yl)thioacetonitrile (10 g).

Workup

  1. filtrationthe precipitate was filtered off
  2. additionthe filtrate was poured into the mixture of water (30 ml) and dichloromethane (300 ml)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel (450 ml)
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b4d42d768bb74af5b094816e47a190c9
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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