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

HRID 1984617

반응식

HRID 1984617 반응식
[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>[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

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 65955Dimiracetam

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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), Cul (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.

후처리

  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

출처 및 근거

ORD 기록
ord-03b91c1a14ed468b9147a4aec5d477a4
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544705B2

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