Thionyl Chloride → 2-(Chloromethyl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1257407Notes

Reaction equation

HRID 1257407 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH2:14]O)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:20])=O>O1CCCC1>[Cl:20][CH2:14][C:11]1[S:12][CH:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2726773HCID 2726773, compound

Product 1

HCID 629239612-(Chloromethyl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (4.14 g) obtained in Example 103a was dissolved in tetrahydrofuran (100 mL), and thionyl chloride (3.5 mL) was added. The reaction mixture was stirred at room temperature for 24 hr, and heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (3.19 g) as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6cbd65fa7c324d4a9109b90d123384b0
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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