N-Iodosuccinimide → (R)-1-(3,5-dichloro-phenyl)-5-iodo-3-methyl-3-(4-trifluoromethoxy-benzyl)-1H-imidazo[1,2-a]imidazol-2-one

HRID 23838ノート

反応式

HRID 23838 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]([CH3:27])([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[N:11]3[CH:28]=[CH:29][N:30]=[C:10]23)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[I:31]N1C(=O)CCC1=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.CCOC(C)=O>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]([CH3:27])([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=3)[N:11]3[C:28]([I:31])=[CH:29][N:30]=[C:10]23)[CH:3]=[C:2]([Cl:1])[CH:7]=1

参加物

6

反応物 3

HCID 120273N-IodosuccinimideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11676886HCID 11676886、化合物

生成物 1

HCID 11585072(R)-1-(3,5-dichloro-phenyl)-5-iodo-3-methyl-3-(4-trifluoromethoxy-benzyl)-1H-imidazo[1,2-a]imidazol-2-one収率 65%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (R)-1-(3,5-dichloro-phenyl)-3-methyl-3-(4-trifluoromethoxy-benzyl)-1H-imidazo[1,2-α]imidazol-2-one (Example 1) (1.54 g, 3.38 mmol) in 30 mL of THF was treated with N-iodosuccinimide (0.846 g, 3.76 mmol) and pyridinium p-toluenesulfonate (0.086 g, 0.37 mmol). The mixture was stirred at room temperature for 17 h, then diluted with EtOAc and washed with 10% Na2S2O3 solution and water. The combined aqueous layers were extracted with 10 mL of EtOAc. The combined organic phases were washed with 25 mL of brine, dried over Na2SO4, filtered and concentrated. The crude orange oil was purified by silica gel chromatography to provide 1.27 g (65%) of (R)-1-(3,5-dichloro-phenyl)-5-iodo-3-methyl-3-(4-trifluoromethoxy-benzyl)-1H-imidazo[1,2-α]imidazol-2-one as an off-white oil (582.0, M+1).

後処理

  1. washwashed with 10% Na2S2O3 solution and water
  2. extractionThe combined aqueous layers were extracted with 10 mL of EtOAc
  3. washThe combined organic phases were washed with 25 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude orange oil was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4a433d0e5d364020830c341a7b89a00f
出典データセット
uspto-grants-2005_02
特許番号
US06852748B1

反応ノート

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