Ethyl Acetate → 1-Phenyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 15111

反応式

HRID 15111 の反応式
[NH:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12.C([O-])([O-])=O.[K+].[K+].I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)(=O)C>CN1CCCC1=O.[Cu]I>[C:18]1([N:1]2[C:5](=[O:6])[CH2:4][N:3]3[C:7](=[O:10])[CH2:8][CH2:9][CH:2]23)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 65955Dimiracetam

生成物 1

HCID 112413861-Phenyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione収率 11.7%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a solution of tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione (1 g, 7.14 mmol; prepared as described in J. Med. Chem. 36, 4214-4220, 1994,) in N-methylpyrrolidone (NMP, 12 cc), CuI (0.2 g, 1.05 mmol), K2CO3 (1 g, 7.14 mmol) and Iodobenzene (5 g, 24.5 mmol) were added under stirring. The suspension was heated in a microwave apparatus (250 Watt) for 45 min. Ethyl acetate was added to the suspension and the solid was filtered. The organic phase was washed with water and the aqueous phase was re-extracted with CH2Cl2. The organic phases were gathered and dried over Na2SO4, filtered and concentrated to dryness. The residue was triturated with isopropyl ether. The solid was filtered, triturated with water and filtered to yield 0.18 g of the title compound, mp=185-188° C.

後処理

  1. temperatureThe suspension was heated in a microwave apparatus (250 Watt) for 45 min
  2. filtrationthe solid was filtered
  3. washThe organic phase was washed with water
  4. extractionthe aqueous phase was re-extracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was triturated with isopropyl ether
  9. filtrationThe solid was filtered
  10. customtriturated with water
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-f942b6681ad44b67b36f20f5a2643d6d
出典データセット
uspto-grants-2010_06
特許番号
US07732473B2

関連ノート

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