Trichloroacetyl isocyanate → HCID 57545312, compound

HRID 2383141Notes

Reaction equation

HRID 2383141 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-])=[CH:14][C:13]3[N:20]=[C:21]([CH2:27][O:28][CH2:29][CH3:30])[N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:35]=C=O)=O.C[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:35])[C:13]3[N:20]=[C:21]([CH2:27][O:28][CH2:29][CH3:30])[N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76400Trichloroacetyl isocyanate2×HCID 10942334Sodium MethoxideHCID 67050974HCID 67050974, compound

Product 1

HCID 57545312HCID 57545312, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A modification of the general method described in Part C of Example 3 was followed using 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline (2.6 g, 6.4 mmol) as the starting material and chloroform as the solvent. The reaction with trichloroacetyl isocyanate was not complete after one hour as evidenced by a TLC analysis. Additional trichloroacetyl isocyanate was added, and the reaction was stirred overnight. Following the reaction with sodium methoxide, the solid product was isolated by filtration and washed with methanol and a mixture of dichloromethane and water. The solid was isolated by filtration and recrystallized from 2-methoxyethyl ether. The crystals were dried under high vacuum to provide 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 183-184° C.

Workup

  1. customthe solid product was isolated by filtration
  2. washwashed with methanol
  3. additiona mixture of dichloromethane and water
  4. customThe solid was isolated by filtration
  5. customrecrystallized from 2-methoxyethyl ether
  6. customThe crystals were dried under high vacuum

Sources & evidence

ORD record
ord-deab99cf6a83477a94e56ccbebd6d7e9
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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