Methyl iodide → HCID 66818221, compound

HRID 1754988Notes

Reaction equation

HRID 1754988 reaction equation
IC.[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([N:11]([CH3:15])[C:12]([NH2:14])=S)=[CH:6][C:5]=1[CH3:16].CO[CH:19](OC)[CH2:20][NH2:21]>CC(C)=O.C(O)C(C)C>[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([N:11]([C:12]2[NH:21][CH:20]=[CH:19][N:14]=2)[CH3:15])=[CH:6][C:5]=1[CH3:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 87166587HCID 87166587, compound

Product 1

HCID 66818221HCID 66818221, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6560IsobutanolSolvent

Procedure

Iodomethane (260 mg, 9.15 mmol) was added to a solution of 1-(4-bromo-3,5-dimethyl-phenyl)-1-methyl-thiourea (500 mg, 1.83 mmol) in acetone (10 ml) with stirring in a nitrogen stream, and the mixture was heated with stirring at 50° C. for two hours. The reaction solution was concentrated under reduced pressure, and a mixture of the resulting residue and aminoacetaldehyde dimethylacetal (250 mg, 2.38 mmol) in iso-BuOH (8.3 ml) was then heated under reflux for four hours. The reaction mixture was concentrated under reduced pressure. Concentrated hydrochloric acid (3 ml) was then added to the resulting residue, and the mixture was heated with stirring at 90° C. for 30 minutes. The reaction mixture was cooled and then adjusted to pH 10 with a 2 N aqueous sodium hydroxide solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-methanol) to give (4-bromo-3,5-dimethyl-phenyl)-(1H-imidazol-2-yl)-methyl-amine (145 mg, 28%).

Workup

  1. temperaturethe mixture was heated
  2. stirringwith stirring at 50° C. for two hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. temperaturewas then heated
  5. temperatureunder reflux for four hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. additionConcentrated hydrochloric acid (3 ml) was then added to the resulting residue
  8. temperaturethe mixture was heated
  9. stirringwith stirring at 90° C. for 30 minutes
  10. temperatureThe reaction mixture was cooled
  11. extractionfollowed by extraction with dichloromethane
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-81d0b12ff20c41d5906b372e22d288cc
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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