Thionyl Chloride → HCID 23149199, compound

HRID 1983064Notes

Reaction equation

HRID 1983064 reaction equation
O[CH2:2][N:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4]1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH2:2][N:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23149157HCID 23149157, compound

Product 1

HCID 23149199HCID 23149199, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

The obtained 1-hydroxymethyl-4-trifluoromethyl-3-ethoxycarbonyl-1H-pyrole was dissolved to 3 ml of chloroform, and 4 ml of thionyl chloride was added, followed by refluxing for 30 minutes. 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 225 mg of 1-chloromethyl-4-trifluoromethyl-3-ethoxycarbonyl-1H-pyrole.

Workup

  1. additionwas added
  2. temperatureby refluxing for 30 minutes
  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-3e3c2a64ab56459f8bb3c94b096bc4ab
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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