Trichloroacetyl isocyanate → HCID 57545307, compound

HRID 2383105Notes

Reaction equation

HRID 2383105 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH2:24][O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:21]([CH2:32][CH2:33][CH2:34][CH3:35])=[N:20][C:14]=3[CH:15]=[N+:16]([O-])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:40]=C=O)=O.C[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH2:24][O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:21]([CH2:32][CH2:33][CH2:34][CH3:35])=[N:20][C:14]=3[C:15]([NH2:40])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 76400Trichloroacetyl isocyanate2×HCID 10942334Sodium MethoxideHCID 67228406HCID 67228406, compound

Product 1

HCID 57545307HCID 57545307, compoundYield 64.3%

Procedure

A modification of the general method described in Part C of Example 3 was used to treat 7-benzyloxy-2-butyl-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline (1.0 g, 2.1 mmol). An analysis by TLC indicated that the reaction with trichloroacetyl isocyanate (1.35 mL, 11.3 mmol) was incomplete after two hours, and additional trichloroacetyl isocyanate (1 mL) was added and stirred for one hour. Following the reaction with sodium methoxide, a tan precipitate formed, and the mixture was stirred over two days. The precipitate was isolated by filtration, recrystallized from ethanol, isolated by filtration, washed with hexanes, and dried overnight in a vacuum oven to provide 0.63 g of 7-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white, crystalline solid, mp 188.0-189.0° C.

Workup

  1. customa tan precipitate formed
  2. stirringthe mixture was stirred over two days
  3. customThe precipitate was isolated by filtration
  4. customrecrystallized from ethanol
  5. customisolated by filtration
  6. washwashed with hexanes
  7. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-725703e132ad470ea079eb2e9e8aebdc
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…