Hydrogen Peroxide → HCID 59323483, compound

HRID 424702Notes

Reaction equation

HRID 424702 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[C:16]([Cl:24])[CH:17]=[C:18]([Cl:23])[CH:19]=2)[NH:14][C:13]=1[S:25][CH3:26])=[O:11].[OH:27]O.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[C:16]([Cl:24])[CH:17]=[C:18]([Cl:23])[CH:19]=2)[NH:14][C:13]=1[S:25]([CH3:26])=[O:27])=[O:11]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 59323484HCID 59323484, compound2×

Product 1

HCID 59323483HCID 59323483, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

6,8-Dichloro-2-methylsulfanyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (2,4-dichloro-phenyl)-amide (Compound 3 in Scheme, 1.13 g, 2.52 mmol) in acetic acid was mixed with 30% hydrogen peroxide (0.57 g, 2 eq) and heated at 70-80° C. for 2 days upon agitation. The reactants were poured into iced water, filtered, washed with water and normal hexane and dried under vacuum. The resultant was used without further purification for next steps (yield: 1.1 g, 94%): 1H NMR (DMSO-d6) δ12.66 (bs, 1H) 8.54-8.19 (m, 4H) 7.61-7.41 (m, 2H) 3.10 (s, 3H)

Workup

  1. filtrationfiltered
  2. washwashed with water and normal hexane
  3. customdried under vacuum
  4. customThe resultant was used without further purification for next steps (yield: 1.1 g, 94%)

Sources & evidence

ORD record
ord-60f65c14406f4d33b737ed4b2471c33b
Source dataset
uspto-grants-2012_01
Patent number
US08106071B2

Reaction notes

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