HCID 20255075, compound → HCID 136161628, compound

HRID 638048Notes

Reaction equation

HRID 638048 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)=[CH:5][CH:4]=1>C(O)(=O)C.Br.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 20255075HCID 20255075, compound

Product 1

HCID 136161628HCID 136161628, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

9.3 g of 2-(4-methoxyphenyl)-1-methyl-4-(trifluoromethyl)-imidazole are dissolved in a mixture of 46.1 ml of acetic acid and 46.5 ml of 48% strength hydrobromic acid and the solution is heated under reflux for 48 hours. The solution is concentrated in a rotary evaporator to form a thick paste which is diluted with water; the pH is adjusted to 11 with concentrated ammonia and finally extraction is carried out several times with ethyl acetate. After drying the organic phase and filtration, concentration is carried out in a rotary evaporator until a thick suspension is produced. After cooling, the suspension is filtered and the crystallisate is dried in vacuo, yielding the 2-(4-hydroxyphenyl)-1-methyl-4-(trifluoromethyl)-1H-imidazole having a melting point of 220°-221°.

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for 48 hours
  3. concentrationThe solution is concentrated in a rotary evaporator
  4. customto form a thick paste which
  5. extractionthe pH is adjusted to 11 with concentrated ammonia and finally extraction
  6. customAfter drying
  7. filtrationthe organic phase and filtration, concentration
  8. customis carried out in a rotary evaporator until a thick suspension
  9. customis produced
  10. temperatureAfter cooling
  11. filtrationthe suspension is filtered
  12. customthe crystallisate is dried in vacuo

Sources & evidence

ORD record
ord-8bc3dd3e51344b6abe9ecf859a0f35d0
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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