Thionyl Chloride → HCID 23149154, compound

HRID 1983060Notes

Reaction equation

HRID 1983060 reaction equation
O[CH2:2][N:3]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4]1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[Cl:13][CH2:2][N:3]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23149123HCID 23149123, compound

Product 1

HCID 23149154HCID 23149154, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The obtained 1-hydroxymethyl-3-nitro-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. The residue was subjected to silica gel column chromatography to obtain 620 mg of 1-chloromethyl-3-nitro-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-76878052cd8647a5bd401fabea433797
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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