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Dichloromethane → 2-cyclopropanecarboxamido-5-Bromo-4-Methyl-3-nitropyridine

HRID 743764
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HRID 743764 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=1.C1(C)C(C)=CC=CC=1.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.ClCCl>CN(C)C1C=CN=CC=1.O>[CH:21]1([C:24]([NH:1][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=2)=[O:25])[CH2:23][CH2:22]1
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참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 7237O-XyleneHCID 77637Cyclopropanecarbonyl chlorideHCID 72132072-Amino-5-bromo-4-methyl-3-nitropyridine

생성물 1

HCID 109794822-cyclopropanecarboxamido-5-Bromo-4-Methyl-3-nitropyridine수율 88.1%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 962Water용매

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온도
110 °C

실험 절차

A mixture comprising 10 g (43.1 mmol) of 2-amino-5-bromo-4-methyl-3-nitropyridine, 6.3 g of 4-dimethylaminopyridine and xylene (50 ml) was heated at 110° C. in a nitrogen atmosphere. 5 g (47.4 mmol) of cyclopropanecarbonyl chloride was dropwise added thereto, followed by further stirring at 110° C. for 2 hours. The reaction mixture was brought to room temperature, followed by the addition of dichloromethane (200 ml) and water (50 ml). The organic phase was separated and the aqueous phase was further extracted with dichloromethane (50 ml). The organic phases were combined and washed with water (50 ml). The resulting organic phase was dried over anhydrous magnesium sulfate and concentrated to give a crude crystal. It was recrystallized from chloroform/ ethyl acetate to give 11.4 g of the title compound (yield 88%).

후처리

  1. customwas brought to room temperature
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was further extracted with dichloromethane (50 ml)
  4. washwashed with water (50 ml)
  5. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude crystal
  8. customIt was recrystallized from chloroform/ ethyl acetate

출처 및 근거

ORD 기록
ord-b53e077efff74a51a0d3e2e1a253e409
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05557002

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