Ammonia → HCID 178488961, compound

HRID 638047Notes

Reaction equation

HRID 638047 reaction equation
C([O-])(=O)C.[NH4+:5].[NH3:6].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.Br[CH:18](Br)[C:19](=O)[C:20]([F:23])([F:22])[F:21]>CO.O>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]2[NH:5][CH:18]=[C:19]([C:20]([F:23])([F:22])[F:21])[N:6]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 312444-MethoxybenzaldehydeHCID 517165Ammonium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetone

Product 1

HCID 178488961HCID 178488961, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

48.1 g of ammonium acetate and 300 ml of concentrated ammonia are added to a solution of 81.6 g of 4-methoxybenzaldehyde in 1.5 liters of methanol and 300 ml of water. 81.0 g of 3,3-dibromotrifluoroacetone are then added dropwise at room temperature and the reaction mixture is subsequently stirred for 18 hours. The methanol is removed in a rotary evaporator, the aqueous emulsion that remains behind is extracted several times with ethyl acetate, the organic phase is dried and concentrated to a small volume. The addition of hexane and cooling in an ice bath causes the product to crystallise. After filtering off and drying in vacuo at 60°, 2-(4-methoxyphenyl)-4-(trifluoromethyl)-imidazole having a melting point of 197°-202° is obtained. (20b) At an internal temperature of 0°-5°, first of all 5.62 g of potassium tert.-butoxide are added to a solution of 11.14 g of 2-(4-methoxyphenyl)-4-(trifluoromethyl)-imidazole in 107 ml of dimethylformamide. After 20 minutes, a solution of 3.8 ml of methyl iodide in 15 ml of dimethylformamide is slowly added, dropwise, while stirring and the reaction mixture is then stirred at room temperature for a further 4 hours. After removing the dimethylformamide in a rotary evaporator, the residue is made into a slurry with water and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate, concentrated to a small volume and hexane is added until crystallisation begins. After filtering and drying in vacuo, 2-(4-methoxyphenyl)-1-methyl-4-(trifluoromethyl)-imidazole having a melting point of 87°-88° is obtained.

Workup

  1. customThe methanol is removed in a rotary evaporator
  2. extractionbehind is extracted several times with ethyl acetate
  3. customthe organic phase is dried
  4. concentrationconcentrated to a small volume
  5. additionThe addition of hexane
  6. temperaturecooling in an ice bath
  7. customto crystallise
  8. filtrationAfter filtering off
  9. customdrying in vacuo at 60°

Sources & evidence

ORD record
ord-147acfcdd3de486f863bf970dd0ad6d8
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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