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Trifluoroacetic acid → 5-Methyl-7-phenyl-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine

HRID 653569
ノート
印刷プレビュー

反応式

HRID 653569 の反応式
C(=O)(O)O.NNC(N)=N.FC(F)(F)C(O)=O.[NH2:17][C:18]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[NH:20][N:19]=1.[C:27]([CH2:35][C:36](=O)[CH3:37])(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl.C(O)(=O)C.C1(C)C=CC=CC=1>[NH2:17][C:18]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[NH:20][N:19]=1.[CH3:37][C:36]1[CH:35]=[C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:19]2[N:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=[C:18]2[N:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6422Trifluoroacetic acidHCID 7166BenzoylacetoneHCID 3508265-(trifluoromethyl)-4H-1,2,4-triazol-3-amineHCID 178513185HCID 178513185、化合物

生成物 2

HCID 3508265-(trifluoromethyl)-4H-1,2,4-triazol-3-amineHCID 27536745-Methyl-7-phenyl-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine
収率 112.7%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

By the procedure reported by V. A. Lopyrev Zh. Obshch. Khim. 53 p. 1684, 1983 (Chemical Abstracts 139865y, 1983) a crude sample of 3-amino-5-trifluoromethyl-1,2,4-triazole was prepared by the cyclocondensation of aminoguanidine bicarbonate with trifluoroacetic acid in refluxing toluene. This material was used effectively without further purification in subsequent ring condensation reactions. To 30 ml. of glacial acetic acid stirring, 3.0 g (19.7 mmol) of 3-amino-5-trifluoromethyl-1,2,4-triazole and 3.5 g (21.6 mmol) of benzoylacetone were added and the mixture heated at reflux for 3 h. A solution soon formed after heating. The solvent was evaporated in vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oily residue. Silica gel column chromatography (methylene chloride) afforded 3.09 g of the title compound which was present as the major component, m.p. 106°-108° C.

後処理

  1. customThis material was used effectively without further purification in subsequent ring condensation reactions
  2. temperaturethe mixture heated
  3. temperatureat reflux for 3 h
  4. customA solution soon formed
  5. temperatureafter heating
  6. customThe solvent was evaporated in vacuo and excess water
  7. additionadded to the residue
  8. extractionfollowed by extraction with 200 ml of ethyl acetate
  9. washThe extract was washed with water, saturated sodium bicarbonate, brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in vacuo
  12. customto give an oily residue

出典と根拠

ORDレコード
ord-ab63506cf30c49d6968d37c95c94bb80
出典データセット
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05127936

反応ノート

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