Pyridine → HCID 68612474, compound

HRID 1848307Notes

Reaction equation

HRID 1848307 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12](=[O:28])[CH2:13][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)(O)[C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.S(Cl)(Cl)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12](=[O:28])[CH:13]=[C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)[C:15]([F:18])([F:16])[F:17])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 68613419HCID 68613419, compound

Product 1

HCID 68612474HCID 68612474, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 5.34 g of toluene to 1.78 g (4.12 mmol) of 1-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one, 0.98 g (8.25 mmol) of thionyl chloride and 0.65 g (8.25 mmol) of pyridine were added at 80° C., and stirred for 3 hours. 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 0.33 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 1.69 g of 1-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one (yield 99.4%).

Workup

  1. additionwere added at 80° C.
  2. customseparated
  3. additionby adding 20 ml of ethyl acetate and 10 ml of water
  4. washAfter washing the ethyl acetate phase with an aqueous solution of 0.33 g of sodium hydroxide
  5. dissolutiondissolved into 10 ml of water
  6. washthe phase was washed with water
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2819c274f4b1454894d8f1132d43179c
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

Loading…