Pyridine → HCID 54063699, compound

HRID 2295252Notes

Reaction equation

HRID 2295252 reaction equation
C[S:2]([CH2:5]CC#N)(=[O:4])=[O:3].P(Cl)(Cl)Cl.[N:13]1C=CC=[CH:15][CH:14]=1.[Cl:19]Cl.[CH2:21]([Cl:23])Cl>>[Cl:19][C:15](=[C:21]([Cl:23])[S:2]([CH3:5])(=[O:3])=[O:4])[C:14]#[N:13]

Participants

6

Reactant 5

HCID 1049Pyridine2×HCID 6344DichloromethaneHCID 24387Phosphorus trichloride2×HCID 24526Chlorine2×HCID 12714644Dapansutrile

Product 1

HCID 54063699HCID 54063699, compoundYield 21%

Procedure

31 g (0.23 mol) of 3-methylsulphonyl-propionitrile were melted at 100° C. in a 100 ml four-necked flask, and 2.2 g of PCl3 and 0.7 g of pyridine were added. 34 g of chlorine (0.48 mol) were then introduced at 100° C. during the course of 7 hours. After further addition of 1.1 g of PCl3 and 0.4 g of pyridine, 10 g of chlorine were again introduced. After cooling, the reaction mixture was diluted with 30 ml of methylene chloride and extracted twice by shaking with 50 ml of water in each case, and the organic phase was concentrated. 30 g of dark brown oil which, after mixing with a little ethanol, cooling and filtering off under suction, gave 9.5 g (21%) of pale crystals, melting point 110° to 114° C., without the yield of mother liquor.

Workup

  1. additionwere again introduced
  2. temperatureAfter cooling
  3. extractionextracted twice
  4. concentrationthe organic phase was concentrated
  5. addition30 g of dark brown oil which, after mixing with a little ethanol
  6. temperaturecooling
  7. filtrationfiltering off under suction

Sources & evidence

ORD record
ord-cfb371dff02e47519acbab71bddaaf1b
Source dataset
uspto-grants-1984_01
Patent number
US04424167

Reaction notes

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