4,4'-Dichlorobenzophenone → 1-(p-Chlorobenzyl)-alpha,alpha-bis-(p-chlorophenyl)imidazole-2-methanol

HRID 261970

반응식

HRID 261970 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:9][CH:8]=1.C([O-])(=O)C([O-])=O.CN(C)CCN(C)C.[Cl:33][C:34]1[CH:48]=[CH:47][C:37]([C:38]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[O:39])=[CH:36][CH:35]=1>CCCCCC.O1CCCC1>[Cl:6][C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:38]([C:37]2[CH:47]=[CH:48][C:34]([Cl:33])=[CH:35][CH:36]=2)([C:40]2[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=2)[OH:39])=[CH:9][CH:8]=1

참가 물질

8

반응물 5

HCID 70344,4'-DichlorobenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 71081OxalateHCID 27791911-(4-chlorobenzyl)-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 124339431-(p-Chlorobenzyl)-alpha,alpha-bis-(p-chlorophenyl)imidazole-2-methanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

In the course of one hour, 64 ml. (0.105 mol) of 15% butyl lithium in n-hexane were added dropwise at -65° to -70° C. and under a nitrogen atmosphere, to a solution of 19.3 g (0.1 mol) of 1-(p-chlorobenzyl)imidazole (prepared from the oxalate described under (A) and 12.2 g (0.105 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml. of anhydrous tetrahydrofuran. The reaction mixture was stirred for one hour and then a suspension of 25.1 g (0.1 mol) of 4,4'-dichlorobenzophenone in 150 ml. of anhydrous tetrahydrofuran was added quickly under the same reaction conditions. Stirring was continued for one hour and then the cooling means was removed and the reaction mixture was kept standing overnight at room temperature. 20 ml. of water were added and the organic phase was separated off and concentrated. The residue was suspended in a mixture of water and diethyl ether. The solid matter formed was filtered off and the ethereal layer was separated off, dried over sodium sulphate and concentrated. The residue was twice crystallised from methanol. 1-(p-Chlorobenzyl)-α,α-bis-(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 171°-173° C.

후처리

  1. customIn the course of one hour, 64 ml
  2. stirringStirring
  3. waitwas continued for one hour
  4. customthe cooling means was removed
  5. waitthe reaction mixture was kept standing overnight at room temperature
  6. additionof water were added
  7. customthe organic phase was separated off
  8. concentrationconcentrated
  9. additionThe residue was suspended in a mixture of water and diethyl ether
  10. customThe solid matter formed
  11. filtrationwas filtered off
  12. customthe ethereal layer was separated off
  13. dry with materialdried over sodium sulphate
  14. concentrationconcentrated
  15. customThe residue was twice crystallised from methanol

출처 및 근거

ORD 기록
ord-d3e6e6039c9e49a0854b0d34e1cf2e96
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

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