Triethylamine → 3-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazole

HRID 1197869

반응식

HRID 1197869 반응식
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17](Cl)[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=2)=[CH:12][CH:11]=1.[C:29]([NH:33][NH2:34])(=O)[CH2:30][CH3:31]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH2:30]([C:29]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[C:17]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=2)=[N:34][N:33]=1)[CH3:31]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 79890PropionylhydrazineHCID 13633435N-(4-methoxyphenyl)-4-nitro-3-methylbenzene carboximidoyl chloride

생성물 1

HCID 191052393-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazole수율 90.1%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 6212Chloroform용매

실험 절차

1.4 ml of triethylamine, then 3 g of the product of Step B were introduced into a solution of 1.76 g of propionic acid hydrazide in 160 ml of toluene, this latter having been brought to reflux and then cooled. After refluxing for 1 hour, the toluene was eliminated under reduced pressure and the residue was taken up in 50 ml of chloroform and 50 ml of water. The aqueous phase was extracted with chloroform and the organic extracts were dried and concentrated to obtain an oil which was purified by chromatography on silica and elution with ethyl acetate and cyclohexane (8-2) to obtain 3 g of 3-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazole in the form of an oil which had an Rf of 0.6 on thin film chromatography (eluent:chloroformethanol 9-1).

후처리

  1. temperatureto reflux
  2. temperaturecooled
  3. temperatureAfter refluxing for 1 hour
  4. extractionThe aqueous phase was extracted with chloroform
  5. customthe organic extracts were dried
  6. concentrationconcentrated
  7. customto obtain an oil which
  8. customwas purified by chromatography on silica and elution with ethyl acetate and cyclohexane (8-2)

출처 및 근거

ORD 기록
ord-e7abdfbe1afa475bad383ea23d5f7867
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278180

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