1-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanone → HCID 71226564, compound

HRID 704955Notes

Reaction equation

HRID 704955 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16](=[O:23])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1.[CH2:24]([Mg]Cl)[CH2:25][CH3:26]>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:16]([OH:23])([CH2:24][CH2:25][CH3:26])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

5

Reactant 2

HCID 157537781-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 178455855HCID 178455855, compound

Product 1

HCID 71226564HCID 71226564, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

MgBr diethyl etherate (10.5 g, 40.2 mmol) was added to a solution of the above-mentioned ethanone (6.0 g, 16.8 mmol) in dichloromethane (DCM, 65 ml) and the mixture stirred at room temperature for about 90 min. This mixture was then cooled to about 0° C. and n-propylmagnesium chloride (22.8 ml of a 2 M solution in THF, 45.6 mmol) was added dropwise. After stirring for about two hours, the mixture was allowed to warm to room temperature and was then quenched by addition of a saturated ammonium chloride solution. The organic components were extracted three times with DCM, the organic phases combined, washed again with saturated ammonium chloride solution, dried and the solvents evaporated. Addition of diisopropyl ether resulted in precipitation of the unreacted starting material, which was filtered off. The filtrate was then purified using reverse phase chromatography, to give the product as a light brown colored solid (2.5 g, 36%, HPLC2 Rt=1.26 min, masse=392).

Workup

  1. temperatureThis mixture was then cooled to about 0° C.
  2. stirringAfter stirring for about two hours
  3. temperatureto warm to room temperature
  4. customwas then quenched by addition of a saturated ammonium chloride solution
  5. extractionThe organic components were extracted three times with DCM
  6. washwashed again with saturated ammonium chloride solution
  7. customdried
  8. customthe solvents evaporated
  9. additionAddition of diisopropyl ether
  10. customresulted in precipitation of the
  11. filtrationwas filtered off
  12. customThe filtrate was then purified

Sources & evidence

ORD record
ord-1ccdf86edd6c4672813d1b26893866d0
Source dataset
uspto-grants-2015_11
Patent number
US09173402B2

Reaction notes

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