Formaldehyde → 1-(2,4-Dichlorophenylmethyl)-4,5-dihydro-2-(1-phenylethenyl)imidazole

HRID 569583Notes

Reaction equation

HRID 569583 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH2:14][CH2:13][N:12]=[C:11]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+].[CH2:24]=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH2:14][CH2:13][N:12]=[C:11]1[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:24]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 138511211-(2,4-Dichlorophenyl)methyl-4,5-dihydro-2-phenylmethylimidazole

Product 1

HCID 138511221-(2,4-Dichlorophenylmethyl)-4,5-dihydro-2-(1-phenylethenyl)imidazoleYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,4-Dichlorophenyl)methyl-4,5-dihydro-2-phenylmethylimidazole (3.19 g, 0.01 mol) was added to a slurry of sodium hydride (80% dispersion in mineral oil, 0.3 g, 0.01 mol) in dry dimethylformamide (15 ml) and the mixture was stirred at room temperature for 30 minutes. Paraformaldehyde (3 g, 0.01 mol) was added to the reaction mixture and the resulting mixture was heated at 70° C. for 6 hours. The reaction mixture was cooled, water was added and the resulting mixture was extracted with ether. The organic phase was separated, washed with brine, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel in ammonia/methanol/ethyl acetate (1:4:45) to yield 1-(2,4-dichlorophenylmethyl)-4,5-dihydro-2-(1-phenylethenyl)imidazole (2.6 g), (δ(CDCl3) 3.3 (2H, t, J=6 Hz), 3.95 (2H, t, J=6 Hz), 4.1 (2H, s), 5.65 (1H, s), 5.8 (1H, s), and 7.0-7.5 (8H, m) p.p.m. having the formula ##STR24##

Workup

  1. temperaturethe resulting mixture was heated at 70° C. for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe resulting mixture was extracted with ether
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was chromatographed on silica gel in ammonia/methanol/ethyl acetate (1:4:45)

Sources & evidence

ORD record
ord-e1dd89889460468a9a6e6e81d4d256f1
Source dataset
uspto-grants-1988_03
Patent number
US04732989

Reaction notes

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