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

HRID 2300042노트

반응식

HRID 2300042 반응식
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:12](=[O:13])[CH2:11][C:9](=[O:10])[N:8]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:6]1=[O:7].N1C=CC=CC=1.[C:26](Cl)(=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29]>ClCCl>[CH3:17][CH:16]([CH3:18])[CH2:15][CH2:14][N:8]1[C:9](=[O:10])[CH:11]([C:26](=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:12](=[O:13])[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6]1=[O:7]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 66054Isovaleryl chlorideHCID 18375361HCID 18375361, 화합물

생성물 1

HCID 98848751,3-Bis(3-methylbutyl)-5-(3-methyl-1-oxobutyl)barbituric acid수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

To a solution of 1,3-bis(3-methylbutyl)barbituric acid 268 mg (1.00 mmol) in dry dichloromethane 3.0 mL under a nitrogen atmosphere, added was pyridine 0.81 mL (0.79 g, 10 mmol, 10 equivalents) and stirred at 0° C. Added was isovaleryl chloride 121 mg (1.00 mmol, 1.00 equivalent) in dichloromethane 1.5 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 4 hours. Added was dichloromethane 40 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 383 mg, after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-bis(3-methylbutyl)-5-(3-methyl-1-oxobutyl)barbituric acid 278 mg as white plates (79.0% yield).

후처리

  1. additionAdded
  2. customof 20 minutes
  3. stirringstirred at room temperature for 4 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)

출처 및 근거

ORD 기록
ord-ae657e249fab442d811d13102449de0b
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498164B1

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