Acetyl chloride → Imiquimod hydrochloride

HRID 1920274Notes

Reaction equation

HRID 1920274 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])[CH:15]=[N:14][C:13]=1[C:21]#[N:22]>C(O)C>[ClH:4].[CH3:20][CH:18]([CH3:19])[CH2:17][N:16]1[C:12]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[C:21]([NH2:22])[C:13]=2[N:14]=[CH:15]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 251645955-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

Product 1

HCID 13982876Imiquimod hydrochlorideYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of acetyl chloride (0.15 mL, 2 mmol) in ethanol (2 mL) was added to a solution of 5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile (0.13 g) in ethanol (5 mL). The mixture was heated at reflux for two hours and allowed to cool to ambient temperature. The volume of the mixture was decreased to 2 mL by concentrating under reduced pressure. A solid was present, and the remaining liquid was decanted away from the solid, which was washed with diethyl ether (2×2 mL) and dried overnight in a vacuum oven at room temperature to provide 0.035 g (23% for Example 19 and Example 20 combined) of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride as a beige solid, mp>265° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for two hours
  3. concentrationby concentrating under reduced pressure
  4. customthe remaining liquid was decanted away from the solid, which
  5. washwas washed with diethyl ether (2×2 mL)
  6. customdried overnight in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-087d5ed3a94740e9abb0728479f19740
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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