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

HRID 261937

반응식

HRID 261937 반응식
[CH3:1][O:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.CN(C)CCN(C)C.C([Li])CCC.[Cl:22][C:23]1[CH:37]=[CH:36][C:26]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1>CCCCCC.O.O1CCCC1>[Cl:22][C:23]1[CH:37]=[CH:36][C:26]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)([C:5]2[N:4]([CH2:3][O:2][CH3:1])[CH:8]=[CH:7][N:6]=2)[OH:28])=[CH:25][CH:24]=1

참가 물질

8

반응물 4

HCID 70344,4'-DichlorobenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 883591-(methoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 12433908alpha,alpha-Bis(p-chlorophenyl)-1-(methoxymethyl)imidazole-2-methanol

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-60 °C

실험 절차

To a solution of 11.2 g. (0.1 mol) of 1-(methoxymethyl)-imidazole and 13.9 g. (0.12 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml. of anhydrous tetrahydrofuran 51 ml. (0.12 mol) of n-butyllithium solution in hexane was added with stirring over a period of about one hour and at a temperature of -60° C. Stirring was continued for another 2 hours at -60° C. Cooling was discontinued and 25.1 g. (0.1 mol) of 4,4'-dichlorobenzophenone in 150 ml. of anhydrous tetrahydrofuran was added drop-wise. The mixture was stirred for 6 hours at room temperature and decomposed by addition of 15 ml. of water. Lithium hydroxide was removed by filtration and the filtrate was concentrated. A 2 N hydrochloric acid solution was added and the mixture was extracted with liberal amounts of diethyl ether. The acidic aqueous solution was made alkaline by addition of potassium carbonate and extracted with diethyl ether, toluene and ethyl acetate. The organic solvent solutions were combined, dried and concentrated. The solid was purified by crystallisation from toluene; its melting point was 145°-146° C.

후처리

  1. stirringStirring
  2. waitwas continued for another 2 hours at -60° C
  3. temperatureCooling
  4. stirringThe mixture was stirred for 6 hours at room temperature
  5. additiondecomposed by addition of 15 ml
  6. customLithium hydroxide was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. additionA 2 N hydrochloric acid solution was added
  9. extractionthe mixture was extracted with liberal amounts of diethyl ether
  10. additionby addition of potassium carbonate
  11. extractionextracted with diethyl ether, toluene and ethyl acetate
  12. customdried
  13. concentrationconcentrated
  14. customThe solid was purified by crystallisation from toluene

출처 및 근거

ORD 기록
ord-65e270d83da04276b7f3ff3d1c3ca2db
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

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