Thionyl Chloride → 1-chloromethyl-3-cyano-1H-pyrole

HRID 1983066Notes

Reaction equation

HRID 1983066 reaction equation
O[CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4]1.S(Cl)([Cl:12])=O>C(Cl)(Cl)Cl>[Cl:12][CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21639436HCID 21639436, compound

Product 1

HCID 231492011-chloromethyl-3-cyano-1H-pyrole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The obtained 1-hydroxymethyl-3-cyano-1H-pyrole was dissolved to 3 ml of chloroform, and 2 ml of thionyl chloride was added, followed by stirring at room temperature for 1 hour. After the reaction mixture was cooled to 0° C., it was poured into ice-water. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography to obtain 290 mg of 1-chloromethyl-3-cyano-1H-pyrole.

Workup

  1. additionwas added
  2. temperatureAfter the reaction mixture was cooled to 0° C.
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50af9075080648de8974223f44402e93
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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