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Methyl morpholine oxide → 3-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

HRID 501442
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HRID 501442 반응식
C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+].C([N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:27])[C:21]=2[N:20]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:19]1=[O:35])C=C>O=[Os](=O)(=O)=O.O.O1CCOCC1>[CH2:28]([N:20]1[C:21]2[C:22]([Cl:27])=[N:23][CH:24]=[CH:25][C:26]=2[NH:18][C:19]1=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
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참가 물질

7

반응물 3

HCID 82029Methyl morpholine oxideHCID 230705921-Allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-oneHCID 23667635Sodium periodate

생성물 1

HCID 230705823-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one수율 58.5%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매
HCID 962
Water
용매
2회
HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

1.5 ml of water, 1.06 g of 4-methyl morpholine N-oxide, 3 ml of an aqueous solution of 2% osmic acid, and a 6 ml aqueous solution of 1.94 g of sodium periodate were added to a 15 ml 1,4-dioxane solution of 0.75 g of 1-allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one, and the mixture was heated at 60° C. for 18 hours. 200 ml of water was added to the solution, and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed twice with 50 ml of water and then washed with 50 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.38 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:1).

후처리

  1. extractionthe mixture was extracted with 100 ml of ethyl acetate
  2. washThe organic layer was washed twice with 50 ml of water
  3. washwashed with 50 ml of a saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-db5c070109a947338be1a59eb67b9434
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772226B2

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