Diphenyl Ether → methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate

HRID 742105노트

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HRID 742105 반응식
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH2:17][C:18]#[CH:19])[CH:6]=1)(=[O:3])[CH3:2].O(C1C=CC=CC=1)C1C=CC=CC=1>>[C:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH2:17][O:16][C:7]=2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[Cl:15])(=[O:3])[CH3:2]

참가 물질

3

반응물 2

HCID 7583Diphenyl EtherHCID 10588933Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

생성물 1

HCID 54402287methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate수율 33.8%

반응 조건

온도
230 °C

실험 절차

A mixture of 40 parts of methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate and 172 parts of phenoxybenzene was stirred for 45 min. at 230° C. After cooling, the reaction mixture was poured into petroleumether. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3). The eluent of the desired fractions was evaporated and the residue was crystallized from acetonitrile, yielding 11.9 parts (33.8%) of methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate (interm. 11).

후처리

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into petroleumether
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3)
  8. customThe eluent of the desired fractions was evaporated
  9. customthe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-46bb7714f9774adf96228bed8780ba9c
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552553

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