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

HRID 1668506Notes

Reaction equation

HRID 1668506 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-283d8ec913ef41e3a40018170ed5eefd
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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