Cleve's acid → HCID 86718861、化合物

HRID 528800

反応式

HRID 528800 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20](Cl)=[O:21]>N1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:13])=[O:14])[CH:8]=[CH:7]2)=[O:21]

参加物

4

反応物 2

HCID 8386Cleve's acidHCID 76403Benzoyl chloride, 3,4-dichloro-

生成物 1

HCID 86718861HCID 86718861、化合物収率 95.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

8-Amino-2-naphthalenesulfonic acid (Aldrich, 1.00 g, 4.48 mmol) and 3,4-dichlorobenzoyl chloride (938 mg, 4.48 mmol) were dissolved in pyridine (10.0 mL), and the resulting reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then concentrated in vacuo, and the residue was dissolved in 1N HCl. The solution was extracted with EtOAc (5×), and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (1.70 g, 91%). 1H NMR (DMSO-d6) δ 11.30 (s, 1H), 8.93 (d, J=2.0 Hz, 1H), 8.83 (s, 1H), 8.65 (dd, J=8.0, 1.9 Hz, 1H), 8.58-8.50 (m, 1H), 8.50-8.43 (m, 2H), 8.34 (dd, J=8.6, 1.5 Hz, 1H), 8.19-8.14 (m, 2H), 6.14 (br s, 1H); MS(ESI−) m/z 394.2 (M−H)−.

後処理

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. dissolutionthe residue was dissolved in 1N HCl
  4. extractionThe solution was extracted with EtOAc (5×)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ac8b2e40277a4b89bd00462279c7a034
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

関連ノート

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