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1,1-Dimethylhydrazine → 6-Methyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamide

HRID 649306
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HRID 649306 반응식
[O:1]=[C:2]([CH2:13][CH2:14][CH3:15])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].CN(C)N>C1(C)C=CC=CC=1>[CH3:15][C:14]1[O:1][C:2]([CH2:13][CH2:14][CH3:15])=[C:3]([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:5])[C:2](=[O:1])[CH:13]=1
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참가 물질

4

반응물 2

HCID 59761,1-DimethylhydrazineHCID 3384353-oxo-N-phenylhexanamide

생성물 1

HCID 138540146-Methyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamide수율 97.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

A mixture of 2.05 g (10 m mol) of 3-oxo-N-phenylhexanamide (m.p. 77.0°-78.5° C.), 0.9 g (15 m mol) of N,N-dimethylhydrazine and 15 ml of toluene was stirred for 8 hours at 60° C. Then, unreacted N,N-dimethylhydrazine and the resulted water, together with about 2 ml of toluene were distilled off outside the reaction system. A solution of 3.90 g (25 m mol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 8 ml of toluene was dropwise added to the remaining solution over a period of 30 minutes, while refluxing. The mixture was further refluxed for 2.5 hours and 3 ml of toluene was distilled off outside the reaction system. The reaction mixture was cooled to room temperature. The resulted crystals were filtered off, washed and dried to obtain 1.32 g (Yield: 49%) of the title compound.

후처리

  1. distillationThen, unreacted N,N-dimethylhydrazine and the resulted water, together with about 2 ml of toluene were distilled off outside the reaction system
  2. additionA solution of 3.90 g (25 m mol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 8 ml of toluene was dropwise added to the remaining solution over a period of 30 minutes
  3. temperaturewhile refluxing
  4. temperatureThe mixture was further refluxed for 2.5 hours
  5. distillation3 ml of toluene was distilled off outside the reaction system
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationThe resulted crystals were filtered off
  8. washwashed
  9. customdried

출처 및 근거

ORD 기록
ord-e69b6b799f154b3c8c2ea2d0f0436dc9
출처 데이터셋
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04739083

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