Ethyl Acetate → 1-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-ol

HRID 25085

반응식

HRID 25085 반응식
C(OCC)(=O)C.Cl(O)(=O)(=O)=O.Cl([O-])(=O)(=O)=O.[CH3:17][CH:18]1[CH2:27][C:26]2[CH:25]=[C:24]3[O:28][CH2:29][O:30][C:23]3=[CH:22][C:21]=2[CH:20]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[OH+:19]1.[NH:40]([C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1)[NH2:41]>C(O)(C)C>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([C:20](=[N:41][NH:40][C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[C:21]2[C:26]([CH2:27][CH:18]([OH:19])[CH3:17])=[CH:25][C:24]3[O:28][CH2:29][O:30][C:23]=3[CH:22]=2)=[CH:32][CH:33]=1)([O-:39])=[O:38]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24247Perchloric AcidHCID 3465582-HydrazinylpyrimidineHCID 131724741(+/-)-7-Methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate

생성물 1

HCID 865938161-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-ol수율 64%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A stirred mixture of 3.29 g (9.99 mmol) of (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochroman-5-ol, 40 ml of ethyl acetate and 1.0 ml (1.15 mmol) perchloric acid was refluxed for 1 h. After cooling the precipitated (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate was filtered off, and it was stirred at reflux temperature with 1.6 g (14.55 mmol) of 2-hydrazinopyrimdine in 50 ml of isopropanol for 2 h, then concentrated. The residue was dissolved in dichloromethane and washed several times with water. After drying and evaporation the crude product was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of toluene-ethyl acetate (0.1:4) as eluent to yield 2.71 g (64%) of the title compound; Mp.: 125-127° C.

후처리

  1. temperaturewas refluxed for 1 h
  2. filtrationwas filtered off
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed several times with water
  6. customAfter drying
  7. customevaporation the crude product
  8. customwas purified by column chromatography
  9. additiona mixture of toluene-ethyl acetate (0.1:4) as eluent

출처 및 근거

ORD 기록
ord-7fd80c4ad35640a5957268fc3f7f7d79
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858605B2

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