N,N,N',N'-Tetramethylethylenediamine → alpha-(2,4-Dichlorophenyl)-alpha-(p-fluorophenyl)-1-(methoxymethyl)imidazole-2-methanol

HRID 261962Notes

Reaction equation

HRID 261962 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.CN(C)CCN(C)C.[Cl:22][C:23]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:24]=1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:26]>O1CCCC1.O>[Cl:22][C:23]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:24]=1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)([C:10]1[N:9]([CH2:8][O:7][CH3:6])[CH:13]=[CH:12][N:11]=1)[OH:26]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 883591-(methoxymethyl)-1H-imidazoleHCID 2847592,4-Dichloro-4'-fluorobenzophenoneHCID 178418339Butyllithium

Product 1

HCID 12433903alpha-(2,4-Dichlorophenyl)-alpha-(p-fluorophenyl)-1-(methoxymethyl)imidazole-2-methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

At -60° C. and under a nitrogen atmosphere, 44 ml. (0.072 mol) of n-butyl lithium (15% solution in n-hexane) was added dropwise under stirring to a solution of 7.8 g (0.07 mol) of 1-(methoxymethyl)imidazole and 8.1 g (0.072 mol) of N,N,N',N'-tetramethylethylenediamine in 100 ml of anhydrous tetrahydrofuran. The mixture was stirred for one hour and then 18.9 g (0.070 mol) of 2,4-dichloro-4'-fluorobenzophenone in 100 ml of anhydrous tetrahydrofuran were added at -60° C. The solution was stirred for one hour at -60° C. and kept standing overnight at room temperature. Then 50 ml of water were added and the solid matter formed was filtered off. The filtrate was extracted with tetrahydrofuran and diethyl ether. The organic phase was dried over sodium sulphate and the solvents were distilled off. Diethyl ether was added to the semisolid residue and the solid matter was filtered off. This product was combined with the solid matter obtained after the addition of water. The substance was twice crystallised from acetone with a small amount of dimethylformamide. α-(2,4-Dichlorophenyl)-α-(p-fluorophenyl)-1-(methoxymethyl)imidazole-2-methanol was obtained. Melting point 179° C.

Workup

  1. customAt -60° C.
  2. stirringThe solution was stirred for one hour at -60° C.
  3. waitkept standing overnight at room temperature
  4. customthe solid matter formed
  5. filtrationwas filtered off
  6. extractionThe filtrate was extracted with tetrahydrofuran and diethyl ether
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. distillationthe solvents were distilled off
  9. additionDiethyl ether was added to the semisolid residue
  10. filtrationthe solid matter was filtered off
  11. customobtained
  12. customThe substance was twice crystallised from acetone with a small amount of dimethylformamide

Sources & evidence

ORD record
ord-feb254dc042b4046a1689ae4b9ce6a4f
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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