Pyridine → HCID 68613686, compound

HRID 1848305Notes

Reaction equation

HRID 1848305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:21]([F:24])([F:23])[F:22])[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)(Cl)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:21]([F:24])([F:23])[F:22])=[CH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([S:19][CH3:20])=[CH:17][CH:18]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 24386Thionyl Chloride2×HCID 68612603HCID 68612603, compound

Product 1

HCID 68613686HCID 68613686, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 1.44 g of toluene to 0.48 g (1.17 mmol) of 3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-(methylthio)phenyl) butan-1-one, 0.28 g (2.34 mmol) of thionyl chloride and 0.19 g (2.34 mmol) of pyridine were added at 80° C., and stirred for 3 hours. The reaction was traced by high-performance liquid chromatography. Since the raw materials did not disappear, 0.14 g (1.17 mmol) of thionyl chloride and 0.09 g (1.17 mmol) of pyridine were added and stirred for 1 hour. The reaction solution was cooled to room temperature, and separated by adding 20 ml of ethyl acetate and 10 ml of water. After washing the ethyl acetate phase with an aqueous solution of 0.14 g of sodium hydroxide dissolved into 10 ml of water, the phase was washed with water. The solvent was distilled off under reduced pressure to obtain 0.37 g of 3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(4-(methylthio)phenyl)-2-buten-1-one (yield 81.8%).

Workup

  1. additionwere added at 80° C.
  2. stirringstirred for 1 hour
  3. customseparated
  4. additionby adding 20 ml of ethyl acetate and 10 ml of water
  5. washAfter washing the ethyl acetate phase with an aqueous solution of 0.14 g of sodium hydroxide
  6. dissolutiondissolved into 10 ml of water
  7. washthe phase was washed with water
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9c390c971f0b4f3aa27e578b5383eef3
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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