Bromine → 1-(4-Amino-3-bromo-5-methylphenyl)-2,4-dimethylimidazole

HRID 2231663Notes

Reaction equation

HRID 2231663 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]2[CH3:16])=[CH:6][C:5]=1[CH3:17].C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:3][C:4]1[C:5]([CH3:17])=[CH:6][C:7]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]2[CH3:16])=[CH:8][C:9]=1[Br:1]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 144502694-(2,4-Dimethyl-1H-imidazol-1-yl)-2-methylaniline

Product 1

HCID 144502861-(4-Amino-3-bromo-5-methylphenyl)-2,4-dimethylimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (5.6 cm3) in glacial acetic acid (50 cm3) was added dropwise over 0.5 hours to a stirred solution of 1-(4-amino-3-methylphenyl)-2,4-dimethylimidazole (20.3 g) and sodium acetate (9.02 g) in glacial acetic acid (200 cm3). After a further 0.5 hours, volatile material was removed in vacuo, and the residue was partitioned between chloroform (200 cm3) and 10% aqueous sodium hydroxide solution (to pH 10). The aqueous phase was further extracted with chloroform (2×100 cm3) and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to afford a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 19:1. Combination and evaporation of the appropriate fractions gave an oil which was triturated with ether to afford the title compound, m.p. 176°-180.5°. The mother liquors were evaporated and the residue was rechromatographed on silica, as before, to give a further crop of material (total yield 17.3 g).

Workup

  1. customvolatile material was removed in vacuo
  2. customthe residue was partitioned between chloroform (200 cm3) and 10% aqueous sodium hydroxide solution (to pH 10)
  3. extractionThe aqueous phase was further extracted with chloroform (2×100 cm3)
  4. dry with materialdried (MgSO4) organic extracts
  5. customwere evaporated in vacuo
  6. customto afford a solid which
  7. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with dichloromethane
  9. customCombination and evaporation of the appropriate fractions
  10. customgave an oil which
  11. customwas triturated with ether

Sources & evidence

ORD record
ord-749c7bc2d3894df18f11ad6f233650ab
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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