Imidazole → 3-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)propanamide

HRID 1393851노트

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HRID 1393851 반응식
[CH3:1][C:2]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14](O)=[O:15])=[CH:8][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.N1C=CN=C1.[H-].[Na+].[NH2:42][C:43]1[S:44][S:45][C:46](=[S:48])[N:47]=1>O1CCCC1.O>[CH3:1][C:2]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([NH:42][C:43]2[S:44][S:45][C:46](=[S:48])[N:47]=2)=[O:15])=[CH:8][CH:7]=1

참가 물질

8

반응물 5

HCID 795Imidazole2회HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 693078643-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}propionic acid

생성물 1

HCID 723564363-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)propanamide수율 59%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

3-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}propionic acid (1.00 g, 3.31 mmol) was dissolved in tetrahydrofuran (11 ml), and 1,1′-carbonyldiimidazole (0.643 g, 3.97 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at 0° C. Sodium hydride (60% oil suspension 0.132 g, 3.31 mmol) was suspended in tetrahydrofuran (11 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.497 g, 3.31 mmol) was added thereto. After being stirred for 30 minutes at 0° C., the reaction mixture, with the imidazole mixture added thereto, was stirred for 2 hours at 0° C. The mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel column chromatography (chloroform), to give 3-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)propanamide (Compound 3) (0.847 g, 59%).

후처리

  1. stirringwas stirred for 2 hours at 0° C
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform)

출처 및 근거

ORD 기록
ord-141fa95257fe4d1fa5d2b2b8582c175b
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348017B2

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