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Potassium Carbonate → {4-[2-Methoxy-4-(methylamino)-5-nitrophenoxy] (2-pyridyl)}-n-methylcarboxamide

HRID 1915676
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HRID 1915676 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[OH:14].CC(C)([O-])C.[K+].Cl[C:22]1C=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C[N:39](C)C(=O)C>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][C:26]1[CH:27]=[CH:22][N:39]=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:25]=1
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참가 물질

6

반응물 5

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 41507923-chloro-N-methylbenzamideHCID 137426772-Methoxy-4-(methylamino)-5-nitrophenolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 131725843{4-[2-Methoxy-4-(methylamino)-5-nitrophenoxy] (2-pyridyl)}-n-methylcarboxamide

실험 절차

To a stirred solution of 2-methoxy-4-(methylamino)-5-nitrophenol (1 eq) in N,N-dimethylacetamide was added potassium-t-butoxide (1.2 eq) and continued stirring at ambient temperature utility solidified. To it was then added (3-chlorophenyl)-N-methylcarboxamide (1 eq) and anhydrous potassium carbonate (1 eq) and the resulting mixture was heated to 50° C. whereby the solid liquified. It was then heated to 110° C. for 12 h. After cooling to ambient temperature the solvent was distilled off and the resulting solid was extracted using ethyl acetate in a soxhlet apparatus for 48 h. The organic layer was cooled to 0° C., when the product crystallized from the ethyl acetate to give {4-[2-methoxy-4-(methylamino)-5-nitrophenoxy](2-pyridyl)}-N-methylcarboxamide. MS: MH+332

후처리

  1. temperatureIt was then heated to 110° C. for 12 h
  2. temperatureAfter cooling to ambient temperature the solvent
  3. distillationwas distilled off
  4. extractionthe resulting solid was extracted
  5. customfor 48 h
  6. temperatureThe organic layer was cooled to 0° C.
  7. customwhen the product crystallized from the ethyl acetate

출처 및 근거

ORD 기록
ord-fdea8cde34214937be1699d0a9bbe409
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08614330B2

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