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

HRID 619927

반응식

HRID 619927 반응식
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

참가 물질

6

반응물 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178509291HCID 178509291, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3bc193ebb6d4773a61dc10ecf9397aa
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818273

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