Sodium Iodide → HCID 70282739, compound

HRID 374988Notes

Reaction equation

HRID 374988 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:9]1([CH2:15][N:16]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:17]2[C:26]3[N:27]=[C:28]([CH2:30][O:31][CH2:32][CH2:33]OS(C)(=O)=O)[NH:29][C:25]=3[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC(C)=O>[C:9]1([CH2:15][N:16]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:17]2[C:26]3[N:27]=[C:28]4[CH2:30][O:31][CH2:32][CH2:33][N:29]4[C:25]=3[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178505310HCID 178505310, compound

Product 1

HCID 70282739HCID 70282739, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Excess potassium carbonate and excess sodium iodide were added to a solution of N,N-bis(phenylmethyl)-2-(2-methylsulfonyloxyethoxy)methyl-1H-imidazo[4,5-c]quinolin-4-amine (0.6 g, 1.14 mmole) in acetone (200 mL). The reaction mixture was heated at reflux overnight then concentrated under vacuum. The residue was partitioned between methylene chloride (150 mL) and water (50 mL). The methylene chloride was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with 10:10:80 v/v/v methylene chloride:ethyl acetate:hexanes) to provide 0.42 g of N,N-bis(phenylmethyl)-10,11-dihydro-8H-[1,4]-oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6amine as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthen concentrated under vacuum
  4. customThe residue was partitioned between methylene chloride (150 mL) and water (50 mL)
  5. customThe methylene chloride was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography (silica gel eluting with 10:10:80 v/v/v methylene chloride:ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-308ea83692134445a0b27be8eec2d0b7
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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