Phenylhydrazine → 5-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1055017노트

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HRID 1055017 반응식
CS/[C:3](=[N:9]\[C:10](=O)[CH:11]=[C:12]([CH3:14])[CH3:13])/[N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH3:13][C:12]([CH3:14])=[CH:11][C:10]1[N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]=[C:3]([N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)[N:9]=1

참가 물질

4

반응물 2

HCID 7516PhenylhydrazineHCID 178503950HCID 178503950, 화합물

생성물 1

HCID 900265325-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole수율 38.9%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-pyrrolidin-1-yl-meth-(Z)-ylideneamide (130 mg, 0.575 mmol) and phenyl hydrazine (0.6 ml, 5.75 mmol) was stirred for 3 hours at 100° C. The mixture was cooled, diluted with ethyl acetate and washed twice with water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography using 50% ethyl acetate in hexane affording 5-(2-methyl-propenyl)-1-phenyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (60 mg, 38.87%) as colorless liquid. MS: m/z=268.8 (M+H+)

후처리

  1. temperatureThe mixture was cooled
  2. washwashed twice with water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-37503e7efce5415699813d66145e4013
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394311B2

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