Water → HCID 178519585、化合物

HRID 64630

反応式

HRID 64630 の反応式
COC(OC)[N:4]1[CH:8]=[CH:7][CH:6]=[N:5]1.C([Li])CCC.[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.O>O1CCCC1.CCCCCC>[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)([C:8]2[CH:7]=[CH:6][NH:5][N:4]=2)[OH:22])=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 70344,4'-DichlorobenzophenoneHCID 136726821-(Dimethoxymethyl)-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 178519585HCID 178519585、化合物収率 29.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A solution of 14.2 g of 1-(dimethoxymethyl)-pyrazole in 125 ml of tetrahydrofuran at -40° C. was treated with 79 ml of a 1.27M solution of n-butyllithium in hexane under a nitrogen atmosphere. When this addition was complete, 25.2 g of 4,4'-dichlorobenzophenone were added. The reaction was stirred for 48 hours allowing the temperature to come to room temperature. The reaction mixture was added to 200 ml of water and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, filtered and evaporated. The semi-solid residue was triturated with toluene. The toluene filtrate was collected and evaporated and the residue therefrom was purified by high pressure liquid chromatography over silica gel. The appropriate fractions were combined and evaporated to provide 9.5 g of the desired title product. Crystallization from 15% ethyl acetate in hexane provided material with a melting point of 138°-140° C. A second recrystallization provided material with the following analysis.

後処理

  1. additionWhen this addition
  2. customto come to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe semi-solid residue was triturated with toluene
  9. customThe toluene filtrate was collected
  10. customevaporated
  11. customthe residue therefrom was purified by high pressure liquid chromatography over silica gel
  12. customevaporated

出典と根拠

ORDレコード
ord-d4ebcca7a8184270be738a504b87086c
出典データセット
uspto-grants-1986_09
特許番号
US04609666

関連ノート

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