Cleve's acid → HCID 86718861, compound

HRID 528800

Reaction equation

HRID 528800 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 86718861HCID 86718861, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-ac8b2e40277a4b89bd00462279c7a034
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Linked notes

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