Pyridine → 1,3-Dibenzyl-5-(2-thienylacetyl)barbituric acid

HRID 2300041

반응식

HRID 2300041 반응식
[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.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](Cl)=[O:37].CCOCC>ClCCl>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]([C:36](=[O:37])[CH2:35][C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)[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

참가 물질

6

반응물 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 1623622-Thiopheneacetyl chlorideHCID 268729Mls002704122

생성물 1

HCID 98890351,3-Dibenzyl-5-(2-thienylacetyl)barbituric acid수율 70.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 1,3-dibenzylbarbituric acid 154 mg (0.500 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 2-thienylacetyl chloride 80 mg (0.50 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 ether 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 216 mg after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-dibenzyl-5-(2-thienylacetyl)barbituric acid 153 mg as yellow viscous oil (56.9% yield).

후처리

  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)

출처 및 근거

ORD 기록
ord-3c1f3b0149b84b2bb77617a4f1ff0a3c
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498164B1

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