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

HRID 1393851ノート

反応式

HRID 1393851 の反応式
[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

参加物

8

反応物 5

HCID 795Imidazole2 回HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 693078643-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}propionic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-141fa95257fe4d1fa5d2b2b8582c175b
出典データセット
uspto-grants-2008_03
特許番号
US07348017B2

反応ノート

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