Hydrogen Bromide → HCID 14450287, compound

HRID 1199539Notes

Reaction equation

HRID 1199539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[CH3:14])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[BrH:19].BrBr>C(O)(=O)C>[Br:19][C:7]1[CH:6]=[C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[CH3:14])[CH:4]=[C:3]([C:15]([F:18])([F:17])[F:16])[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 14450271HCID 14450271, compound

Product 1

HCID 14450287HCID 14450287, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

1-(4-Amino-3-trifluoromethylphenyl)-2,4-dimethylimidazole (10 g) was dissolved in glacial acetic acid (70 cm3). A solution of 45% w/w hydrogen bromide in glacial acetic acid (7.4 cm3) was added. A solution of bromine (2.1 cm3) in glacial acetic acid (30 cm3) was then added dropwise. The mixture was heated at 70° for 3 hours, cooled, concentrated to a small volume by evaporation in vacuo, and basified to pH 8 by addition of aqueous sodium carbonate solution. The aqueous phase was extracted with chloroform (3×200 cm3) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]), eluting with ethyl acetate. Combination and evaporation of appropriate fractions afforded 1-(3-bromo-4-amino-5-trifluoromethylphenyl)-2,4-dimethylimidazole (4.76 g), a small sample of which was recrystallized from ethyl acetate/hexane, m.p. 149°.

Workup

  1. temperatureThe mixture was heated at 70° for 3 hours
  2. temperaturecooled
  3. concentrationconcentrated to a small volume by evaporation in vacuo
  4. additionbasified to pH 8 by addition of aqueous sodium carbonate solution
  5. extractionThe aqueous phase was extracted with chloroform (3×200 cm3)
  6. dry with materialthe combined organic extracts were dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting with ethyl acetate
  10. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-2017e91a5b9d40098e0f308174b1dc1e
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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