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

HRID 2051033

反応式

HRID 2051033 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 21584188Chloroform methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-049ccdb15aaf4163924d80045ee0f16c
出典データセット
uspto-grants-1991_05
特許番号
US05015742

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