P-Phenylenediamine → HCID 57756220、化合物

HRID 227827

反応式

HRID 227827 の反応式
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][N:11]=1>O>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:7][C:4]3[CH:5]=[CH:6][C:1]([NH2:8])=[CH:2][CH:3]=3)=[N:11][N:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 7814P-PhenylenediamineHCID 2721091-Chloro-4-phenylphthalazine

生成物 1

HCID 57756220HCID 57756220、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

Benzene-1,4-diamine (0.337 g, 3.12 mmol) and 1-chloro-4-phenylphthalazine (0.500 g, 2.08 mmol) were treated with 7.5 mL 2-BuOH in a sealed tube and heated to 110° C. The reaction quickly became a solid, yellow mass. After several hours, the reaction was cooled and diluted with water. The slurry was then partitioned between DCM and 1N NaOH. The aqueous layer was extracted into DCM (2×). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography, ISCO, 40 g, 0-10% MeOH/MC to give N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as an orange-brown solid. MS m/z=313 [M+H]+. Calc'd for C20H16N4: 312.4.

後処理

  1. customThe reaction
  2. waitAfter several hours
  3. temperaturethe reaction was cooled
  4. customThe slurry was then partitioned between DCM and 1N NaOH
  5. extractionThe aqueous layer was extracted into DCM (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting material was purified by silica gel chromatography, ISCO, 40 g, 0-10% MeOH/MC

出典と根拠

ORDレコード
ord-6075b051e6e9493d9a18c6d2569faf92
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

関連ノート

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