Nitric Acid → 3-methyl-4-phenyl-4H-1,2,4-triazole

HRID 1759034

반응식

HRID 1759034 반응식
[C:1]1([N:7]=[C:8]=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([NH:13][NH2:14])(=O)[CH3:11].[N+]([O-])(O)=O.[OH-].[NH4+]>C(O)C>[CH3:11][C:10]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:14][N:13]=1

참가 물질

6

반응물 4

HCID 944Nitric Acid3회HCID 7673Phenyl Isothiocyanate2회HCID 14039Acetohydrazide2회HCID 14923Ammonium Hydroxide

생성물 1

HCID 122169083-methyl-4-phenyl-4H-1,2,4-triazole

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2.5 mol of phenyl isothiocyanate (Formula XXI of Chart B) is added to 0.5 mol of acethydrazide (Formula IV of Chart B) in 500 ml of absolute ethanol and refluxed for one hour, cooled and filtered. This is then dissolved in a solution of 28.0 gm sodium hydroxide in 400 ml of water and the mixture is refluxed for two hours. The reaction mixture is cooled in an ice bath and treated with 100 ml of concentrated hydrochloric acid. The resulting solid is filtered and recrystallized. 66.7 mmol of the solid is added to 53 ml of 20% nitric acid and heated on a steam bath. When the vigorous exothermic reaction is complete, an additional 53 ml of 20% nitric acid is added, and an additional 66.7 mmol of previous solid. Portions of the solid are reacted with nitric acid until all of the previous solid is reacted. After the final addition the reaction mixture is heated twenty minutes on a steam bath, cooled to ambient temperature and poured into cold 15% aqueous ammonium hydroxide solution. The subtitled product is extracted with chloroform, dried and concentrated to yield 3-methyl-4-phenyl-4H-1,2,4-triazole, (Formula XXIV, Chart B) mp 109°-111° C.

후처리

  1. temperaturerefluxed for one hour
  2. temperaturecooled
  3. filtrationfiltered
  4. dissolutionThis is then dissolved in a solution of 28.0 gm sodium hydroxide in 400 ml of water
  5. temperaturethe mixture is refluxed for two hours
  6. temperatureThe reaction mixture is cooled in an ice bath
  7. additiontreated with 100 ml of concentrated hydrochloric acid
  8. filtrationThe resulting solid is filtered
  9. customrecrystallized
  10. temperatureheated on a steam bath
  11. customWhen the vigorous exothermic reaction
  12. customis reacted
  13. additionAfter the final addition the reaction mixture
  14. temperatureis heated twenty minutes on a steam bath
  15. extractionThe subtitled product is extracted with chloroform
  16. customdried
  17. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ee4e0a37541a4d8489efcb2602a43d99
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04338453

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