Potassium hydride → 4-(2,2-dimethyl-1-oxopropyl)-N-[4-(2,2-dimethyl-1-oxopropyl)-benzoyl]benzamide

HRID 1768669ノート

反応式

HRID 1768669 の反応式
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[H-].[K+].[H][H].[CH3:20][C:21]([CH3:34])([CH3:33])[C:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)=[O:23]>O1CCCC1.CCCCCC>[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:11][C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([C:22](=[O:23])[C:21]([CH3:20])([CH3:33])[CH3:34])=[CH:32][CH:31]=2)=[O:10])=[CH:7][CH:6]=1)=[O:4]

参加物

7

反応物 4

HCID 82127Potassium hydrideHCID 105362344-(2,2-Dimethyl-1-oxopropyl)-benzamideHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-HCID 178418361HCID 178418361、化合物

生成物 1

HCID 98007244-(2,2-dimethyl-1-oxopropyl)-N-[4-(2,2-dimethyl-1-oxopropyl)-benzoyl]benzamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

4.2 grams (20.5 mmoles) of 4-(2,2-dimethyl-1-oxopropyl) benzamide is dissolved in 100 milliliters of dry tetrahydrofuran. The solution is cooled to 0° C., and 3.7 grams (22.6 mmoles) of potassium hydride (from a 24.5% mixture in mineral oil) which has been washed free of oil with hexane, is added. After hydrogen evolution has ceased, (approximately 2 hours), a solution of 4.6 grams (20.5 mmoles) of 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride in 20 milliliters of dry tetrahydrofuran is added dropwise at 0° C. When addition is complete, the reaction mixture is concentrated in vacuo, and the residue is then dissolved in methylene dichloride and filtered to remove solids. The filtrate is purified by flash chromatography (3 inch column and 0.3% then 1% methanol/methylene chloride to elute) and crystallized from diethyl ether to yield the title product (m.p. 131°-132° C.).

後処理

  1. additionis added
  2. custom, (approximately 2 hours),
  3. additionis added dropwise at 0° C
  4. additionWhen addition
  5. concentrationthe reaction mixture is concentrated in vacuo
  6. dissolutionthe residue is then dissolved in methylene dichloride
  7. filtrationfiltered
  8. customto remove solids
  9. customThe filtrate is purified by flash chromatography (3 inch column and 0.3%
  10. wash1% methanol/methylene chloride to elute) and
  11. customcrystallized from diethyl ether

出典と根拠

ORDレコード
ord-c881b126b3004ca1929902fc5ee5105c
出典データセット
uspto-grants-1995_01
特許番号
US05378728

反応ノート

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