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

HRID 261970

反応式

HRID 261970 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3e6e6039c9e49a0854b0d34e1cf2e96
出典データセット
uspto-grants-1979_05
特許番号
US04152441

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