Trichloroacetyl isocyanate → HCID 57545335, compound

HRID 2383103Notes

Reaction equation

HRID 2383103 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)[CH:21]=[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:36]=C=O)=O.C[O-].[Na+]>C(Cl)(Cl)Cl>[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)[CH:21]=[N:20][C:14]=3[C:15]([NH2:36])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76400Trichloroacetyl isocyanateHCID 10942334Sodium MethoxideHCID 67050956HCID 67050956, compound

Product 1

HCID 57545335HCID 57545335, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A modification of the general method described in Part C of Example 3 was used to treat 7-benzyloxy-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline (1.59 g, 3.86 mmol). Chloroform (10 mL) was added to help keep the starting material in solution. The reaction with trichloroacetyl isocyanate (0.6 mL, 5 mmol) was stirred for 4.5 hours. Following the reaction with sodium methoxide, a tan precipitate formed, which was isolated by filtration, washed with hexanes, and dried overnight in a vacuum oven. The solid was then stirred with water overnight, isolated by filtration, and dried in a vacuum oven to provide 0.94 g of 7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 200.3-200.9° C.

Workup

  1. customa tan precipitate formed
  2. customwhich was isolated by filtration
  3. washwashed with hexanes
  4. customdried overnight in a vacuum oven
  5. stirringThe solid was then stirred with water overnight
  6. customisolated by filtration
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-edbaee9cb3d64a1fbd5a687a94b5be12
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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