Sodium Carbonate → HCID 20141773, compound

HRID 649538Notes

Reaction equation

HRID 649538 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]([CH3:38])[N:24]([C:26]3[CH:27]=[C:28]4[C:33](=[C:34]([CH3:36])[CH:35]=3)[NH:32][C:31](=[O:37])[CH:30]=[CH:29]4)[CH:25]=2)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:12][S:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]([CH3:38])[N:24]([C:26]3[CH:27]=[C:28]4[C:33](=[C:34]([CH3:36])[CH:35]=3)[NH:32][C:31](=[O:37])[CH:30]=[CH:29]4)[CH:25]=2)=[CH:17][CH:16]=1)(=[O:9])=[O:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 20141779HCID 20141779, compound

Product 1

HCID 20141773HCID 20141773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

meta-Chloroperbenzoic acid (0.11 g) was added to a stirred solution of 6-(4-[4-methylsulphinylphenyl]-2-methyl-imidazol-1-yl)-8-methyl-2-(1H)-quinolone (0.14 g) in dichloromethane (20 cm3) at room temperature. After 30 minutes the mixture was poured into saturated sodium carbonate solution (30 cm3) and extracted with dichloromethane (3×30 cm3). The combined and dried (MgSO4) extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:dichloromethane, 1:19 by volume. Collection and evaporation of appropriate fractions afforded a solid which was recrystallised from ethyl acetate to give the title compound, m.p. 345°-7° (0.06 g).

Workup

  1. extractionextracted with dichloromethane (3×30 cm3)
  2. dry with materialdried (MgSO4) extracts
  3. customwere evaporated in vacuo
  4. customto give a residue which
  5. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washeluting with methanol
  7. customCollection and evaporation of appropriate fractions
  8. customafforded a solid which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-41c67297c3fb463faab7aed441e33f8b
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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