Trichloroacetyl isocyanate → HCID 57538842, compound

HRID 2105492Notes

Reaction equation

HRID 2105492 reaction equation
[CH2:1]([C:5]1[N:6]([O:18][CH3:19])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].ClC(Cl)(Cl)C([N:24]=C=O)=O.C[O-].[Na+]>>[CH2:1]([C:5]1[N:6]([O:18][CH3:19])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:24])[C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 76400Trichloroacetyl isocyanateHCID 10942334Sodium MethoxideHCID 67506136HCID 67506136, compound

Product 1

HCID 57538842HCID 57538842, compoundYield 28%

Procedure

The methods described in Parts C and D of Example 20 were used to oxidize and aminate 2-butyl-1-methoxy-1H-imidazo[4,5-c]quinoline (3.2 g, 12.5 mmol) with the following modifications. The oxidation reaction was stirred for two hours at room temperature. The reaction with trichloroacetyl isocyanate (2.2 mL, 19 mmol) was carried out at room temperature overnight, and the reaction sodium methoxide was stirred overnight and then concentrated under reduced pressure. The residue was treated with methanol (5 mL) to form a solid, which was collected by filtration and recrystallized from methanol/water and dried overnight in a vacuum oven at 70° C. to provide 0.946 g of 2-butyl-1-methoxy-1H-imidazo[4,5-c]quinolin-4-amine as golden crystals, mp 197-199° C.

Workup

  1. customThe oxidation reaction
  2. waitwas carried out at room temperature overnight
  3. stirringwas stirred overnight
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with methanol (5 mL)
  6. customto form a solid, which
  7. filtrationwas collected by filtration
  8. customrecrystallized from methanol/water
  9. customdried overnight in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-969789d85d4b49b3a91f454b55873da7
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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