Hydrochloric Acid → 5-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione

HRID 1857509노트

반응식

HRID 1857509 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20](/[CH:21]=[CH:22]/[CH:23]=O)=[CH:19][CH:18]=1.[O:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1.Cl>O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[CH:22][CH:23]=[C:31]2[O:27][C:28](=[O:33])[NH:29][C:30]2=[O:32])=[CH:25][CH:26]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 15485649(E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde

생성물 1

HCID 570370095-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione수율 34.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of (E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde (1.20 g), 2,4-oxazolidinedione (0.525 g), piperidine (0.09 g) and ethanol (20 ml) was heated for 5 hours under reflux. The reaction mixture was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and, then, concentrated. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (50:1) was obtained 5-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione (0.51g, 34%). Recrystallization from dichloromethane-methanol gave pale yellow prisms, m.p.213-214° C.

후처리

  1. temperaturewas heated for 5 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of a silica gel column chromatography
  8. washFrom the fractions eluted with chloroform-methanol (50:1)

출처 및 근거

ORD 기록
ord-099744c7160b44198edfebd72e90bc50
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147099

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