Thionyl Chloride → 1-chloromethyl-3-cyano-4-trifluoromethyl-1H-pyrole

HRID 1983062Notes

Reaction equation

HRID 1983062 reaction equation
O[CH2:2][N:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]#[N:13])=[CH:4]1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:2][N:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]#[N:13])=[CH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 231491381-hydroxymethyl-3-cyano-4-trifluoromethyl-1H-pyrole

Product 1

HCID 231491561-chloromethyl-3-cyano-4-trifluoromethyl-1H-pyrole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The obtained 1-hydroxymethyl-3-cyano-4-trifluoromethyl-1H-pyrole was dissolved to 3 ml of chloroform, and 3 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 to obtain 800 mg of 1-chloromethyl-3-cyano-4-trifluoromethyl-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-5f3391c69aca4f1d92ae41066add774a
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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