Sodium Carbonate → HCID 66620473, compound

HRID 415548Notes

Reaction equation

HRID 415548 reaction equation
[CH3:1][C@@H:2]1[N:6]2[C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=[CH:9][C:8]=3[N:17]=[C:5]2[N:4]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]1[N:6]2[C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N+:10]([O-:33])=[CH:9][C:8]=3[N:17]=[C:5]2[N:4]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 66619934HCID 66619934, compound

Product 1

HCID 66620473HCID 66620473, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate (1.16 g, 3.58 mmol) was dissolved in 50 mL of CHCl3 and treated with MCPBA (1.05 g, 77% max). After 18 hours, the reaction was treated with 20 mL of 1% Na2CO3 solution and the layers were separated. The aqueous layer was extracted with CHCl3 (6×20 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give tert-butyl (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate 5-oxide (1.22 g) as a brown foam.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with CHCl3 (6×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a1e92c8cb2b4cdc8c133d360dfe4112
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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