1,2-Cyclohexanedione → HCID 67378017, 화합물

HRID 877468노트

반응식

HRID 877468 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[NH:10]N.[CH2:12]1[CH2:19][C:17](=O)[C:15](=[O:16])[CH2:14][CH2:13]1>CO>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]2[C:5]=1[C:13]1[CH2:12][CH2:19][CH2:17][C:15](=[O:16])[C:14]=1[NH:10]2

참가 물질

4

반응물 2

HCID 130061,2-CyclohexanedioneHCID 3084937(2,5-Dichlorophenyl)hydrazine monohydrochloride

생성물 1

HCID 67378017HCID 67378017, 화합물수율 98.4%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

(2,5-Dichlorophenyl)hydrazine hydrochloride (0.3 g, 1.40 mmol) was dissolved in MeOH (3 mL) and 1,2-cyclo hexadione (0.15 g, 1.40 mmol) was added and the mixture heated to 60° C. for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was diluted with water, neutralized with NaHCO3 solution and extracted with EtOAc (3×15 mL). The combined organic extracts were concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to provide the title compound (0.35 g, 11.8%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.92 (bs, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 3.36 (t, J=6.2 Hz, 2H), 2.69 (t, J=6.0 Hz, 2H), 2.34-2.21 (m, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc (3×15 mL)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customto give the crude compound which
  7. customwas purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant]

출처 및 근거

ORD 기록
ord-2165e8e3a3f74a0db088aa7960597654
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987319B2

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