Pyridine → 1,3-Dibenzyl-5-(3-methyl-1-oxobutyl)barbituric acid

HRID 2300039

反応式

HRID 2300039 の反応式
[CH2:1]([N:8]1[C:15](=[O:16])[CH2:14][C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:30](Cl)(=[O:35])[CH2:31][CH:32]([CH3:34])[CH3:33]>ClCCl>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]([C:30](=[O:35])[CH2:31][CH:32]([CH3:34])[CH3:33])[C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 66054Isovaleryl chlorideHCID 268729Mls002704122

生成物 1

HCID 99304081,3-Dibenzyl-5-(3-methyl-1-oxobutyl)barbituric acid収率 88.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

To a solution of 1,3-dibenzyl barbituric acid 265 mg (0.859 mmol) in dry dichloromethane 2.0 mL under a nitrogen atmosphere, added was pyridine 1.0 mL (12 mmol) and stirred at 0° C. Added was isovaleryl chloride 104 mg (0.858 mmol, 1.00 equivalent) in dichloromethane 1.0 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 3 hours. Added was dichloromethane 50 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 351 mg, after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-dibenzyl-5-(3-methyl-1-oxobutyl)barbituric acid 299 mg as colorless viscous oil at first, and in 2 days it turned white plates (88.7% yield).

後処理

  1. additionAdded
  2. customof 20 minutes
  3. stirringstirred at room temperature for 3 hours
  4. additionAdded
  5. washwashed the organic layer with 2 M hydrochloric acid and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customPurified
  8. customafter removal of the solvent under the reduced pressure
  9. washby column chromatography (silica gel, eluted with dichloromethane)

出典と根拠

ORDレコード
ord-7c68d978fa0d4479a28bcfcc33bcd5c9
出典データセット
uspto-grants-2002_12
特許番号
US06498164B1

関連ノート

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