Methane → Imiquimod

HRID 2056962Notes

Reaction equation

HRID 2056962 reaction equation
[CH3:1][CH:2]([CH2:4][N:5]1[C:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[N:16]=[C:17]([NH2:18])[C:8]=2[N:7]=[CH:6]1)[CH3:3].Cl.C.[NH4+].[OH-]>S(S([O-])=O)([O-])=O.[Na+].[Na+].O>[CH2:4]([N:5]1[C:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[N:16]=[C:17]([NH2:18])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 297Methane3×HCID 14923Ammonium HydroxideHCID 13982876Imiquimod hydrochloride

Product 1

HCID 57469ImiquimodYield 80.6%

Reagents, catalysts & solvents 2

HCID 24489Sodium DithioniteCatalystHCID 962WaterSolvent

Conditions

Temperature
87.5 °C

Procedure

100 ml water and 10 g crude Imiquimod HCl are loaded into a 250 ml reactor. The mixture is heated to 85-90° C. to obtain a solution. 0.2 g sodium hydrosulfite is added and the solution turns from orange to yellow. 1 g of charcoal is added and after 10 minutes at 90-95° C. the charcoal is filtered off and the cake is washed with 10 ml of hot water. To the pale yellow solution obtained, 1 g of charcoal is added and stirred for 10 minutes at 90-95° C. The charcoal is filtered off and the cake is washed with 10 ml hot water. To the colorless solution obtained, 3 g NH4OH(NH3 26%) is added at 80° C. The white suspension obtained is cooled to 20° C. and filtered. The cake is washed three times with 10 ml water. No chloride should be detected by silver nitrate during the washes. The solid is dried under vacuum at 50° C. for 10 hours. A 7 g solid is obtained and the yield is 80.5%.

Workup

  1. customto obtain a solution
  2. filtrationis filtered off
  3. washthe cake is washed with 10 ml of hot water
  4. customTo the pale yellow solution obtained
  5. filtrationThe charcoal is filtered off
  6. washthe cake is washed with 10 ml hot water
  7. customTo the colorless solution obtained
  8. customThe white suspension obtained
  9. temperatureis cooled to 20° C.
  10. filtrationfiltered
  11. washThe cake is washed three times with 10 ml water
  12. customThe solid is dried under vacuum at 50° C. for 10 hours

Sources & evidence

ORD record
ord-2b5d3fdc9777410795e07927cdaf2890
Source dataset
uspto-grants-2008_02
Patent number
US07335772B2

Reaction notes

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