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

HRID 653569
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HRID 653569 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

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

생성물 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
수율 112.7%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab63506cf30c49d6968d37c95c94bb80
출처 데이터셋
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05127936

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