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Triethylamine → 5,6-Dihydropyrrolo[1,2-c]imidazol-7-one

HRID 724208
ノート
印刷プレビュー

反応式

HRID 724208 の反応式
O[CH2:2][CH2:3][C:4]([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)=[O:5].C(N(CC)CC)C.CS(Cl)(=O)=O>C(OCC)(=O)C>[CH:10]1[N:9]=[CH:8][N:7]2[CH2:2][CH2:3][C:4](=[O:5])[C:6]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 218796303-Hydroxy-1-(1-trityl-1H-imidazol-4-YL)propan-1-one

生成物 1

HCID 111709605,6-Dihydropyrrolo[1,2-c]imidazol-7-one収率 45.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

3-Hydroxy-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (129 g) was dissolved in ethyl acetate (2 L). While stirring under ice-cooling (ice-salt), triethylamine (65.8 ml) was added and then a solution of methanesulfonyl chloride (34.2 ml) in ethyl acetate (50 ml) was added. The mixture was stirred at the same temperature for 1 h and ice water (0.8 L) was added to the reaction mixture, which was followed by partitioning. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in acetonitrile (2.36 L) and the mixture was stirred at 70° C. for 3 h. The reaction mixture was allowed to assume room temperature. Methanol (0.8 L) and triethylamine (61 ml) were added and the mixture was stirred again at 70° C. for 1.5 h. The solvent was evaporated under reduced pressure and ethyl acetate (200 ml) was added to the resulting residue. The insoluble material was filtered off. The solvent was evaporated and the residue was purified by silica gel column chromatography (eluent; methanol/ethyl acetate; 1/24–1/9). The eluate was recrystallized from methanol/ethyl acetate to give the title compound (18.84 g) as pale brown crystals.

後処理

  1. additionwas added
  2. stirringThe mixture was stirred at the same temperature for 1 h
  3. customby partitioning
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in acetonitrile (2.36 L)
  8. stirringthe mixture was stirred at 70° C. for 3 h
  9. customto assume room temperature
  10. additionMethanol (0.8 L) and triethylamine (61 ml) were added
  11. stirringthe mixture was stirred again at 70° C. for 1.5 h
  12. customThe solvent was evaporated under reduced pressure and ethyl acetate (200 ml)
  13. additionwas added to the resulting residue
  14. filtrationThe insoluble material was filtered off
  15. customThe solvent was evaporated
  16. customthe residue was purified by silica gel column chromatography (eluent; methanol/ethyl acetate; 1/24–1/9)
  17. customThe eluate was recrystallized from methanol/ethyl acetate

出典と根拠

ORDレコード
ord-c74f5503c4864076b56db7b1ccaa7206
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141598B2

反応ノート

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