Ammonia → 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide

HRID 2372396노트

반응식

HRID 2372396 반응식
C(O[C:4](=[N:14][CH3:15])[CH2:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13])C.[C:16]([NH2:22])(=[O:21])[C:17]([NH:19][NH2:20])=O.N>CN1CCOCC1.ClCCl>[F:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([F:13])[C:6]=1[CH2:5][C:4]1[N:14]([CH3:15])[C:17]([C:16]([NH2:22])=[O:21])=[N:19][N:20]=1

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 68200Oxamic acid hydrazideHCID 199042321-ethoxy-2-(2,6-difluorophenyl)-1-(N-methylimino)-ethane

생성물 1

HCID 199042355-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 79724-Methylmorpholine용매

실험 절차

320 mg (1.5 mmol) of 1-ethoxy-2-(2,6-di-fluorophenyl)-1-(N-methylimino)-ethane and 155 mg (1.5 mmol) of oxalic acid monoamide monohydrazide are dissolved under a nitrogen atmosphere in 5 ml of N-methylmorpholine and the whole is heated under reflux for 41 hours After cooling, the reaction mixture is diluted with 20 ml of dichloromethane and extracted by shaking in succession twice with water, twice with 2N hydrochloric acid and again with water. The last three acidic aqueous phases obtained are combined, rendered alkaline with concentrated ammonia solution and extracted three times with dichloromethane. The combined organic phases are dried over magnesium sulphate and concentrated. Recrystallisation of the crude product from ethanol yields 102 mg (27% of the theoretical yield) of the desired 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide which melts at 189-190°.

후처리

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 41 hours
  3. temperatureAfter cooling
  4. extractionextracted
  5. customThe last three acidic aqueous phases obtained
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organic phases are dried over magnesium sulphate
  8. concentrationconcentrated
  9. customRecrystallisation of the crude product from ethanol
  10. customyields 102 mg (27% of the

출처 및 근거

ORD 기록
ord-f0c7dd9575124ad7b62dfe1b077f302b
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05098922

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