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

HRID 441144노트

반응식

HRID 441144 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-464de602b62a40318145e82262907cbf
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521314

반응 노트

불러오는 중…