m-Chloroperbenzoic acid → HCID 20150458, compound

HRID 568352Notes

Reaction equation

HRID 568352 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:31])=[O:9])=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54544996HCID 54544996, compound

Product 1

HCID 20150458HCID 20150458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of m-chloroperbenzoic acid (0.56 g) in dichloromethane (5 cm3) was added dropwise at -70° to a stirred solution of 2-methoxy-6-[4-methylthiophenyl]quinoline (0.7 g) in dichloromethane (10 cm3). The mixture was warmed to room temperature over 1 hour, taken into dichloromethane (25 cm3) and washed with sodium carbonate solution (10 cm3). The organic phase was dried (MgSO4) and evaporated and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform:methanol, 19:1. The appropriate fractions were combined and evaporated to give a solid which was recrystallised from acetone-hexane to afford the title compound, m.p. 163.5°-165.5°, (0.55 g).

Workup

  1. washwashed with sodium carbonate solution (10 cm3)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  5. washeluting with chloroform
  6. customevaporated
  7. customto give a solid which
  8. customwas recrystallised from acetone-hexane

Sources & evidence

ORD record
ord-ad478823544541609541984aac280eed
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

Loading…