1,2-Cyclohexanedione → HCID 67378017、化合物

HRID 877468ノート

反応式

HRID 877468 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 67378017HCID 67378017、化合物収率 98.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

(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).

後処理

  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]

出典と根拠

ORDレコード
ord-2165e8e3a3f74a0db088aa7960597654
出典データセット
uspto-grants-2015_03
特許番号
US08987319B2

反応ノート

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