Tetrahydrofuran → 2-Benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

HRID 1898809ノート

反応式

HRID 1898809 の反応式
N[C:2]1[C:3]2[N:4]([N:10]=[C:11]([S:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=2)[C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].N(OC(C)(C)C)=O.O1CCCC1>CCOCC>[CH2:14]([S:13][C:11]1[N:12]=[C:3]2[CH:2]=[C:7]([Cl:8])[CH:6]=[C:5]([Cl:9])[N:4]2[N:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 10906Tert-Butyl nitriteHCID 190807338-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

生成物 1

HCID 190807782-Benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

8-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine (25.8 g, 0.079 mol), t-butyl nitrite (18.9 mL, 16.4 g, 0.158 mol) and tetrahydrofuran (1.5 L) were combined and heated at reflux with stirring. Gas evolution began immediately and stopped after a few minutes, but the reaction was heated at reflux for an hour. The volatiles were removed by evaporation under reduced pressure and the residue obtained was chromatographed on silica gel eluting with dichloromethane. The product fractions were concentrated by evaporation under reduced pressure and the residue obtained was mixed with ether. The insoluble solid material was collected by filtration. The ether filtrate was concentrated by evaporation under reduced pressure and the residue was rechromatographed on silica gel eluting with 10 percent ethyl acetate in hexane. The product fractions were concentrated by evaporation under reduced pressure and the residue obtained was combined with the insoluble solid material obtained before to obtain 12.2 g (50 percent of theory) of the title compound as a red-brown powder melting at 88°-89° C.

後処理

  1. temperatureheated
  2. temperatureat reflux
  3. waitstopped after a few minutes
  4. temperaturethe reaction was heated
  5. temperatureat reflux for an hour
  6. customThe volatiles were removed by evaporation under reduced pressure
  7. customthe residue obtained
  8. customwas chromatographed on silica gel eluting with dichloromethane
  9. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  10. customthe residue obtained
  11. filtrationThe insoluble solid material was collected by filtration
  12. concentrationThe ether filtrate was concentrated by evaporation under reduced pressure
  13. customthe residue was rechromatographed on silica gel eluting with 10 percent ethyl acetate in hexane
  14. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  15. customthe residue obtained
  16. customobtained before

出典と根拠

ORDレコード
ord-ff9cd4ed5e334f97bc863e1d7f1ef1fc
出典データセット
uspto-grants-1996_11
特許番号
US05571775

反応ノート

読み込み中…