Dimethylamine → 6-(Dimethylamino)-7-methyl-2,3-dihydro-1H-pyrrolo [1,2-a]benzimidazole-5,8-dione

HRID 2051033

Reaktionsgleichung

Reaktionsgleichung von HRID 2051033
[CH3:1][C:2]1[C:13](=[O:14])[C:6]2[N:7]3[CH2:12][CH2:11][CH2:10][C:8]3=[N:9][C:5]=2[C:4](=[O:15])[CH:3]=1.[CH3:16][NH:17][CH3:18].CCCCCC.[K+].[Br-]>CN(C=O)C.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[CH3:16][N:17]([CH3:18])[C:3]1[C:4](=[O:15])[C:5]2[N:9]=[C:8]3[CH2:10][CH2:11][CH2:12][N:7]3[C:6]=2[C:13](=[O:14])[C:2]=1[CH3:1]

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 8058HexaneHCID 253877Potassium BromideHCID 102198607-Methyl-2,3-dihydro-1H-pyrrolo[1,2-a] benzimidazole-5,8-dione

Produkt 1

HCID 156611726-(Dimethylamino)-7-methyl-2,3-dihydro-1H-pyrrolo [1,2-a]benzimidazole-5,8-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.24 mmol) of 26 in 3 mL of dry DMF, chilled to 0° C., was added an excess of methanolic dimethylamine. After the addition, the reaction mixture was stirred at room temperature for about 30 min and then the solvent was evaporated in vacuo. The residue was chromatographed on silica gel employing chloroform as the eluant. The blue-colored 27 was obtained in 42 mg (71%) yield. An analytical sample was prepared by dissolving the residue in a small amount of chloroform, adding hexane, and then chilling the mixture overnight in the refrigerator: mp 158° C. dec; TLC (chloroform/methanol[90:10]), Rf =0.56, IR(KBr pellet) 1675, 1659, 1623, 1524, 1314, 1067 cm-1 ; 1H NMR (CDCl3) δ4.16 (2 H, t, J~7 Hz, C(1) methylene), 3.04 (6 H, s, dimethylamino), 2.87 (2 H, t, J~7 Hz, C(3) methylene), 2.64 (2 H, quintet, J~7 Hz, C(2) methylene); 1.93 (3 H, s, 7-methyl); mass spectrum (EI mode) m/z 245 (P+), 230 (P+ -CH3), 217 (P+ -CO). Anal. Calcd for C13H15N3O2.0.25: C, 62.50; H, 6.15; N, 16.82. Found: C, 62.78; H, 6.32; N, 16.64.

Aufarbeitung

  1. additionAfter the addition
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel
  4. customThe blue-colored 27 was obtained in 42 mg (71%)
  5. customyield
  6. customAn analytical sample was prepared
  7. temperaturechilling the mixture overnight in the refrigerator

Quellen und Nachweise

ORD-Eintrag
ord-049ccdb15aaf4163924d80045ee0f16c
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05015742

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