N-(4-(2,2-Dicyanoethenyl)phenyl)acetamide → N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide

HRID 1668506

반응식

HRID 1668506 반응식
[Na].[NH2:2][C:3]([NH2:5])=[S:4].[C:6]([C:8]([C:20]#[N:21])=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)#[N:7]>C(O)C>[NH2:21][C:20]1[C:8]([C:6]#[N:7])=[C:9]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[NH:2][CH:3]([SH:4])[N:5]=1

참가 물질

5

반응물 3

HCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamideHCID 2723790ThioureaHCID 5360545Sodium

생성물 1

HCID 86621820N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide수율 41.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 20 mL of absolute ethanol, 250 mg of metallic sodium was added in small portions. After dissolved completely, 760 mg of thiourea was added to the above solution, and the mixture was stirred at room temperature for 1 hour. To the reaction, 2.11 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide was added, and the mixture was heated to reflux for 3 hours. Then, the solvent was removed under reduced pressure from the reaction mixture, the residue was dissolved in 30 mL of water. In addition, the mixture was acidified by adding acetic acid in small portions, thereto 30 mL of ethyl acetate was added and then the solution was stirred overnight. Filtration of the precipitated material gave 1.2 g of N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide as a white powder.

후처리

  1. dissolutionAfter dissolved completely
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 hours
  5. customThen, the solvent was removed under reduced pressure from the reaction mixture
  6. dissolutionthe residue was dissolved in 30 mL of water
  7. additionby adding acetic acid in small portions
  8. addition30 mL of ethyl acetate was added
  9. stirringthe solution was stirred overnight
  10. filtrationFiltration of the precipitated material

출처 및 근거

ORD 기록
ord-283d8ec913ef41e3a40018170ed5eefd
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989446B2

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