Dimethyl malonate → 2-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 649451ノート

反応式

HRID 649451 の反応式
C[O-].[Na+].[C:4]([O:11]C)(=O)[CH2:5][C:6](OC)=[O:7].[NH2:13][C:14]1[N:18]=[C:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:16][N:15]=1>CO.C(O)C>[CH2:20]([S:19][C:17]1[N:18]=[C:14]2[N:13]=[C:4]([OH:11])[CH:5]=[C:6]([OH:7])[N:15]2[N:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178509291HCID 178509291、化合物

生成物 1

HCID 1785166162-benzylsulfanyl-7-hydroxy-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one収率 127.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

A solution of 125 g (0.58 mol) of a 25% solution of sodium methoxide in methanol dissolved in 100 ml of absolute ethanol was treated with 66.3 ml (0.29 mol) of dimethyl malonate followed by 60.0 g (0.20 mol) of 3-amino-5-benzylthio-1,2,4-triazole. The resulting solution was heated at reflux for 5 days. On cooling to room temperature the solid which had separated was collected by filtration, washed with cold ethanol and dissolved in 1000 ml of water. The resulting yellow solution was acidified with concentrated HCl to precipitate a solid. The solid was collected by filtration and dried to yield 70.1 g (82%) of the desired product as a white solid, m.p. 199°-210° C. (decomposition). IR and 1H NMR spectra were in agreement with the assigned structure.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 5 days
  3. customhad separated
  4. filtrationwas collected by filtration
  5. washwashed with cold ethanol
  6. dissolutiondissolved in 1000 ml of water
  7. customto precipitate a solid
  8. filtrationThe solid was collected by filtration
  9. customdried

出典と根拠

ORDレコード
ord-4593af937ad34aeda8ffb24643ecda38
出典データセット
uspto-grants-1988_04
特許番号
US04740233

反応ノート

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