2-Bromotoluene → 1-o-tolyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 15112

반응식

HRID 15112 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+].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].C(OCC)(=O)C>CN1CCCC1=O.[Cu]I>[C:19]1([CH3:24])[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12

참가 물질

7

반응물 4

HCID 72362-BromotolueneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 65955Dimiracetam

생성물 1

HCID 117363641-o-tolyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione수율 15.4%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione (1.3 g, 9.28 mmol, prepared as described in J. Med. Chem. 36,4214, 1994) in N-methylpyrrolidone (NMP, 12 cc), CuI (0.5 g, 2.62 mmol), K2CO3 (1.3 g, 9.28 mmol) and 2-bromotoluene (6 g, 35 mmol) were added under stirring. The suspension was heated in a microwave apparatus (250 Watt) for 1 h. 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 Et2O. The solid was filtered, and crystallized the first time with iPrOH and then with AcOEt to yield 0.33 g of the title compound, mp=138-139° C.

후처리

  1. temperatureThe suspension was heated in a microwave apparatus (250 Watt) for 1 h
  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 Et2O
  9. filtrationThe solid was filtered
  10. customcrystallized the first time with iPrOH

출처 및 근거

ORD 기록
ord-a5af9ae55cd3492eb5a25286165b4309
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732473B2

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