Hydrochloric Acid → 1-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanone

HRID 1770364Notes

Reaction equation

HRID 1770364 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:14][C:13]=1[Cl:26])=[O:11].Cl>C1COCC1.O>[Cl:26][C:13]1[CH:14]=[C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:16]=[CH:17][C:12]=1[C:10](=[O:11])[CH2:9][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 24721199HCID 24721199, compound

Product 1

HCID 157537781-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanoneYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1,2,4-Triazole (249 g) was added carefully (small portions) to a mixture of sodium hydride (85 g) in THF (6000 mL). After 30 minutes a solution of 2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (1322 g) in THF (500 mL) was slowly added and the mixture was stirred for 150 min. The pH was adjusted to 7 with dil. hydrochloric acid whereupon water was added (3000 mL). The precipitate was filtered off and washed with MTBE. The organic phase was then concentrated and the resulting solid was filtered off to yield the desired material (1008 g).

Workup

  1. additionwas added (3000 mL)
  2. filtrationThe precipitate was filtered off
  3. washwashed with MTBE
  4. concentrationThe organic phase was then concentrated
  5. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-b4dc4fa4b836422680bd5a51fce98bcc
Source dataset
uspto-grants-2016_02
Patent number
US09247747B2

Reaction notes

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