Acetamidine monohydrochloride → 5-(3-bromo-4-methylphenyl)-2-methyl-1H-imidazole

HRID 1619150Notes

Reaction equation

HRID 1619150 reaction equation
C(=O)(O)[O-].[K+].Cl.[C:7](=[NH:10])([NH2:9])[CH3:8].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([Br:22])[CH:16]=1)=O>O1CCCC1.O>[Br:22][C:17]1[CH:16]=[C:15]([C:13]2[NH:9][C:7]([CH3:8])=[N:10][CH:12]=2)[CH:20]=[CH:19][C:18]=1[CH3:21]

Participants

6

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 516893Potassium Bicarbonate2×HCID 126224992-Bromo-1-(3-bromo-4-methylphenyl)ethanone

Product 1

HCID 581704635-(3-bromo-4-methylphenyl)-2-methyl-1H-imidazoleYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Potassium bicarbonate (2.10 g, 20.7 mmol) was added portionwise to a solution of acetimidamide hydrochloride (1.06 g, 11.2 mmol) in tetrahydrofuran (20 mL) and water (5 mL). The resulting mixture was heated to reflux and 2-bromo-1-(3-bromo-4-methylphenyl)ethanone (preparation 58a, 2.74 g, 9.4 mmol) was added dropwise over a period of 20 minutes. After 3 hours, further acetamidamide hydrochloride (1.06 g, 11.2 mmol) and potassium bicarbonate (1.03 g, 10.1 mmol) were added and the was mixture refluxed overnight. The mixture was evaporated to dryness and partitioned between 2M aqueous hydrochloric acid and ethyl acetate. The acidic aqueous layer was bascified with solid sodium hydroxide and extracted with ethyl acetate. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give a semi solid. This semi solid was heated in vacuo at 70° C. for one hour in order to remove excess acetamidamide to give the pure title compound (0.10 g, 5%) as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperaturethe was mixture refluxed overnight
  4. customThe mixture was evaporated to dryness
  5. custompartitioned between 2M aqueous hydrochloric acid and ethyl acetate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customto give a semi solid
  10. customto remove excess acetamidamide

Sources & evidence

ORD record
ord-c2e7c353795a4bc6bf3d8a9af71cdafa
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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