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

HRID 543305Notes

Reaction equation

HRID 543305 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, 0.1 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 (CDC13) 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 ##STR25##

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-2ac3af2fc3ae49679df3dcc22d7026ad
Source dataset
uspto-grants-1987_04
Patent number
US04661602

Reaction notes

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