Pyridine → HCID 68612576, compound

HRID 1848303Notes

Reaction equation

HRID 1848303 reaction equation
[N:1]1([C:6]2[CH: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[CH:7]=[CH:8][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:10][CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 68612538HCID 68612538, compound

Product 1

HCID 68612576HCID 68612576, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 6.00 g of toluene to 2.00 g (4.65 mmol) of 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one, 1.11 g (9.30 mmol) of thionyl chloride and 0.74 g (9.30 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 50 ml of chloroform and 20 ml of water. After washing the organic phase with an aqueous solution of 0.37 g of sodium hydroxide dissolved into 2.0 g of water, then the phase was washed with water. The solvent was distilled off under reduced pressure to obtain 1.58 g of 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one (Yield 82.4%). Here, the target compound obtained in this Synthesis Example is a mixture of geometric isomers whose ratio determined by 1H-NMR was 4 to 1. 1H-NMR data of mainly produced geometric isomer are shown below.

Workup

  1. additionwere added at 80° C.
  2. customseparated
  3. additionby adding 50 ml of chloroform and 20 ml of water
  4. washAfter washing the organic phase with an aqueous solution of 0.37 g of sodium hydroxide
  5. dissolutiondissolved into 2.0 g of water
  6. washthe phase was washed with water
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-919a9cd9dd664888bdea8dc2d2d65a4d
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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