Ethanol → HCID 54345449, compound

HRID 1872612Notes

Reaction equation

HRID 1872612 reaction equation
C(OO)(=[O:3])C.[C:6]1([CH:12]=[CH:13][C:14]2[S:15][C:16]3[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:26]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)C>C(OC)(=O)C>[C:6]1([CH:12]=[CH:13][C:14]2[S:15][C:16]3[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N+:19]([O-:3])=[CH:18][C:17]=3[N:26]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6585Peracetic AcidHCID 57263972HCID 57263972, compound

Product 1

HCID 54345449HCID 54345449, compound

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent

Procedure

Peracetic acid (1.32 mL of 32% in acetic acid) was added to a suspension of 2-(2-phenyl-1-ethenyl)thiazolo[4,5-c]quinoline (1.20 g) in methyl acetate (50 mL). A precipitate formed. Ethanol was added to the reaction mixture until all of the precipitate was dissolved. The reaction mixture was heated at reflux overnight and then cooled to ambient temperature. The resulting precipitate was isolated by filtration, dried and then recrystallized from methanol/dichloromethane to provide 2-(2-phenyl-1-ethenyl)thiazolo[4,5-c]quinoline-5-oxide as a yellow solid, m.p. 268-270° C. Analysis: Calculated for: C18H12N2OS: % C, 71.03; % H, 3.97; % N, 9.20; Found: % C, 69.94; % H, 3.87; % N, 9.05.

Workup

  1. customA precipitate formed
  2. dissolutionwas dissolved
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. customThe resulting precipitate was isolated by filtration
  6. customdried
  7. customrecrystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-316dbad9ae8745748426113dc82a0278
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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