2,6-Dichloropyridine → 2-Chloro-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine

HRID 443011ノート

反応式

HRID 443011 の反応式
[H-].[Na+].[CH3:3][N:4]1[C:8]([OH:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[N:5]1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=1>CN(C)C(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:9][C:8]2[N:4]([CH3:3])[N:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=2)[N:16]=1

参加物

5

反応物 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 178481859HCID 178481859、化合物

生成物 1

HCID 217146352-Chloro-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒3 回

反応条件

温度
135 °C

実験手順

1.8 g (71 mmol) of sodium hydride (95 percent) was suspended in 25 ml of N,N-dimethylacetamide. A solution of 12.46 g (67 mmol) of 1-methyl-5-hydroxy-3-(trifluoromethyl)pyrazole (J Heterocycl. Chem. 1990, 27, 243) in 40 ml of N,N-dimethylacetamide was added dropwise over 1 hour at 22° C. The resulting solution was added dropwise over 3 hours, under nitrogen, to a solution of 18.5 g (125 mmol) of 2,6-dichloropyridine in 37.5 ml of N,N-dimethylacetamide, heated to 135° C. After a further 5 hours of reaction time, the mixture was cooled to room temperature, the sodium chloride which had precipitated out was filtered off and the filtrate was concentrated. The residue was taken up with toluene and water and the organic phase was washed with saturated sodium chloride solution and concentrated. The solid residue was distilled under vacuum. The title compound distills at 175° C. under 25 mbar. This gave 12.5 g of crude product in the form of a yellow solid (96 percent pure, GC). This was purified by recrystallization from diisopropyl ether. The yield was 11.55 g (62 percent) of colorless crystals, content (GC): 99.9 percent. Other data concerning the product was:

後処理

  1. customAfter a further 5 hours of reaction time
  2. temperaturethe mixture was cooled to room temperature
  3. customthe sodium chloride which had precipitated out
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated
  6. washthe organic phase was washed with saturated sodium chloride solution
  7. concentrationconcentrated
  8. distillationThe solid residue was distilled under vacuum
  9. distillationThe title compound distills at 175° C. under 25 mbar
  10. customThis was purified by recrystallization from diisopropyl ether

出典と根拠

ORDレコード
ord-ed0edd7cd4ba4c5596997e0f87d0b660
出典データセット
uspto-grants-1999_04
特許番号
US05892032

反応ノート

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