Acetyl chloride → HCID 66985921, compound

HRID 1920258

Reaction equation

HRID 1920258 reaction equation
C([Cl:4])(=O)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:15]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:14][C:13]=1[C:25]#[N:26]>C(O)C>[ClH:4].[CH2:21]([C:15]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[C:25]([NH2:26])[C:13]=2[N:14]=1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 585001415-(2-aminophenyl)-2-butyl-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

Product 1

HCID 66985921HCID 66985921, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a solution of acetyl chloride (412 mg, 5.25 mmol) in anhydrous ethanol (17.5 mL) was stirred for 15 minutes. 5-(2-Aminophenyl)-2-butyl-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile (1.04 g, 3.50 mmol) was added, and the reaction was heated at reflux under nitrogen for 21.5 hours, allowed to cool to room temperature overnight, and further cooled on an ice bath. A solid was present and was isolated by filtration, washed with diethyl ether, and air-dried to provide 1.04 g (89%) of 2-butyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under nitrogen for 21.5 hours
  3. temperaturefurther cooled on an ice bath
  4. customwas isolated by filtration
  5. washwashed with diethyl ether
  6. customair-dried

Sources & evidence

ORD record
ord-902cef0a699149f0a3f75385d66559ff
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Linked notes

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