Piperidine → HCID 86750612、化合物

HRID 977277ノート

反応式

HRID 977277 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH:25]=O)=[CH:17][CH:16]=1.[O:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH:25]=[C:31]2[O:27][C:28](=[O:33])[NH:29][C:30]2=[O:32])=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 19965664HCID 19965664、化合物

生成物 1

HCID 86750612HCID 86750612、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of (E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4-pentadien-1-al (2.3 g), 2,4-oxazolidinedione (2.0 g), piperidine (0.596 g) and acetic acid (50 ml) was refluxed under heating conditions for 15 hours. The reaction mixture was concentrated; water was added to the residue, followed by acidification with 2N HCl and subsequent extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to silica gel chromatography to yield 5-[(E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4pentadienylidene]-2,4-oxazolidinedione [mixture of the (E)- and (Z)-configurations](1.0 g, 33%) from the fraction eluted with chloroform-ethyl acetate (9:1, v/v), which was then recrystallized from chloroform-methanol to yield light yellow prisms having a melting point of 208°-210° C.

後処理

  1. temperaturewas refluxed under heating conditions for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the residue
  4. extractionfollowed by acidification with 2N HCl and subsequent extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-096c911feb6d42fc8fe5ca836e370b58
出典データセット
uspto-grants-1997_03
特許番号
US05614544

反応ノート

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