4,4'-Dichlorobenzophenone → alpha,alpha-Bis(p-chlorophenyl)-1-vinylimidazole-2-methanol

HRID 261965

Reaction equation

HRID 261965 reaction equation
C([Li])CCC.[CH:6]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[CH2:7].CN(C)CCN(C)C.[Cl:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CCCCCC.C(O)(=O)C.O.O1CCCC1>[Cl:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)([C:9]2[N:8]([CH:6]=[CH2:7])[CH:12]=[CH:11][N:10]=2)[OH:27])=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 70344,4'-DichlorobenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 661711-VinylimidazoleHCID 178418339Butyllithium

Product 1

HCID 330103alpha,alpha-Bis(p-chlorophenyl)-1-vinylimidazole-2-methanol

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

At a temperature of -60° to -70° C. and under a nitrogen atmosphere, 25 ml. (0.04 mol) of 15% butyl lithium in n-hexane were added to a solution of 3.2 g (0.034 mol) of 1-vinylimidazole and 4.6 g (0.04 mol) of N,N,N',N'-tetramethylethylenediamine in 75 ml. of anhydrous tetrahydrofuran. The mixture was stirred for 2 hours and then 8.5 g (0.034 mol) of 4,4'-dichlorobenzophenone, dissolved in 75 ml. of anhydrous tetrahydrofuran were added dropwise under the same conditions. The reaction mixture was stirred for 2 hours at -60° to -70° C. and kept standing overnight at room temperature under the nitrogen atmosphere. Then 25 ml. of water and a small amount of acetic acid were added to the reaction mixture and the liquid was distilled off. Water was added to the residue and the solid matter was filtered off. The product was crystallised from a mixture of isopropyl alcohol, dimethylformamide and petroleum ether (boiling range 60°-80° C.). α,α-Bis(p-chlorophenyl)-1-vinylimidazole-2-methanol was obtained. Melting point 173.5°-174° C.

Workup

  1. customAt a temperature of -60° to -70° C.
  2. stirringThe reaction mixture was stirred for 2 hours at -60° to -70° C.
  3. waitkept standing overnight at room temperature under the nitrogen atmosphere
  4. distillationthe liquid was distilled off
  5. additionWater was added to the residue
  6. filtrationthe solid matter was filtered off
  7. customThe product was crystallised from a mixture of isopropyl alcohol, dimethylformamide and petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-ace8f163315147b0bb5f02f0e3712f50
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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