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

HRID 1075415노트

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HRID 1075415 반응식
[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

참가 물질

5

반응물 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 178481859HCID 178481859, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매3회

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온도
135 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-143e16c430634f0ab2479f6015236c09
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05900484

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