Ammonia → alpha,alpha-Bis(p-chlorophenyl)-1-(methoxymethyl)-4,5-dimethylimidazole-2-methanol

HRID 261951Notes

Reaction equation

HRID 261951 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[CH:10]1.CN(C)CCN(C)C.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1.N>O1CCCC1>[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)([C:10]2[N:9]([CH2:8][O:7][CH3:6])[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=2)[OH:30])=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 70344,4'-DichlorobenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 213213081-(Methoxymethyl)-4,5-dimethylimidazoleHCID 178418339Butyllithium

Product 1

HCID 12433910alpha,alpha-Bis(p-chlorophenyl)-1-(methoxymethyl)-4,5-dimethylimidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At a temperature of -60° C. and under a nitrogen atmosphere, 114 ml. (0.24 mol) of butyllithium solution (20% in hexane) were added drop-wise with stirring to a solution of 28 g. (0.20 mol) of 1-(methoxymethyl)-4,5-dimethylimidazole and 28 g. (0.24 mol) of N,N,N',N'-tetramethylethylenediamine in 200 ml. of anhydrous tetrahydrofuran. After 2 hours stirring, 50 g. (0.20 mol) of 4,4'-dichlorobenzophenone in 250 ml of anhydrous tetrahydrofuran were added drop-wise at -60° C. After being kept standing overnight, the reaction mixture was extracted with water and the organic phase was concentrated by distilling off the solvents. The residue was treated with 2 N hydrochloric acid and diethyl ether, which resulted in the formation of an organic and aqueous layer with an oily intermediate layer. The aqueous and oily layers were made alkaline with ammonia and extracted with diethyl ether. The extract was dried over sodium sulphate and the solvent was distilled off. The oily residue was thrice recrystallised from isopropyl alcohol. α,α-Bis(p-chlorophenyl)-1-(methoxymethyl)-4,5-dimethylimidazole-2-methanol was obtained. Melting point 151° C.

Workup

  1. customAt a temperature of -60° C.
  2. stirringAfter 2 hours stirring
  3. extractionthe reaction mixture was extracted with water
  4. concentrationthe organic phase was concentrated
  5. distillationby distilling off the solvents
  6. additionThe residue was treated with 2 N hydrochloric acid and diethyl ether, which
  7. customresulted in the formation of an organic and aqueous layer with an oily intermediate layer
  8. extractionextracted with diethyl ether
  9. dry with materialThe extract was dried over sodium sulphate
  10. distillationthe solvent was distilled off
  11. customrecrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-547f966556234a8d96bd5da76264c1fe
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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