Triethylamine → 1-(2,3,5,6-Tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonyloxymethylcarbonylamino-4-nitropyrazole

HRID 257318노트

반응식

HRID 257318 반응식
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[C:11]([F:14])[C:10]([C:15]([F:18])([F:17])[F:16])=[C:9]([F:19])[C:8]=2[F:20])[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].C(N(CC)CC)C.[C:31]([O:34][CH2:35][C:36](Cl)=[O:37])(=[O:33])[CH3:32]>O1CCCC1>[F:20][C:8]1[C:9]([F:19])=[C:10]([C:15]([F:17])([F:18])[F:16])[C:11]([F:14])=[C:12]([F:13])[C:7]=1[N:6]1[C:2]([NH:1][C:36]([CH2:35][O:34][C:31]([CH3:32])=[O:33])=[O:37])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 26297Acetoxyacetyl chloride2회HCID 139337135-Amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-4-nitropyrazole

생성물 1

HCID 197830571-(2,3,5,6-Tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonyloxymethylcarbonylamino-4-nitropyrazole수율 12.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 0.68 gram (0.0020 mole) of 5-amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-4-nitropyrazole and 0.42 gram (0.0042 mole) of triethylamine in 20 mL of tetrahydrofuran was added dropwise a solution of 0.55 gram (0.0040 mole) of acetoxyacetyl chloride in 8 mL of tetrahydrofuran. The reaction mixture was heated at reflux for two hours. An additional 0.43 gram of acetoxyacetyl chloride and 0.22 gram of triethylamine were added, and the mixture was heated at reflux for 20 minutes. The mixture was cooled and filtered,, and the filtrate was evaporated under reduced pressure, leaving an oil. This oil was purified by column chromatography on silica gel, eluted with ethyl acetate/n-hexane (50:50) to yield 0.11 gram of 1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonyloxymethylcarbonylamino-4-nitropyrazole as a waxy solid, Compound 14 of Table 1. The nmr spectrum was consistent with the proposed structure.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 20 minutes
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. customthe filtrate was evaporated under reduced pressure
  8. customleaving an oil
  9. customThis oil was purified by column chromatography on silica gel
  10. washeluted with ethyl acetate/n-hexane (50:50)

출처 및 근거

ORD 기록
ord-43820e121e7c4adbaed624d45dd67672
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262382

반응 노트

불러오는 중…