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

HRID 261965

반응식

HRID 261965 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-ace8f163315147b0bb5f02f0e3712f50
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

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