Cleve's acid → HCID 86718861, 화합물

HRID 528800

반응식

HRID 528800 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 86718861HCID 86718861, 화합물수율 95.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-ac8b2e40277a4b89bd00462279c7a034
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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