Water → 7-Methyl-2,3-dihydro-1H-pyrrolo[1,2-a] benzimidazole-5,8-dione

HRID 2051032

反応式

HRID 2051032 の反応式
N[C:2]1[C:10]2[N:9]=[C:8]3[CH2:11][CH2:12][CH2:13][N:7]3[C:6]=2[CH:5]=[C:4]([CH3:14])[CH:3]=1.P([O-])([O-])([O-])=[O:16].[K+].[K+].[K+].[O]N(S(=O)([O-])=O)S(=O)([O-])=O.[K+].[K+].[K+].[Br-].[OH2:37]>C(Cl)(Cl)Cl.CO>[CH3:14][C:4]1[C:5](=[O:37])[C:6]2[N:7]3[CH2:13][CH2:12][CH2:11][C:8]3=[N:9][C:10]=2[C:2](=[O:16])[CH:3]=1

参加物

7

反応物 5

HCID 962Water2 回HCID 62657Potassium Phosphate, Tribasic2 回HCID 253877Potassium BromideHCID 3032624Potassium nitrosodisulfonateHCID 156611712,3-Dihydro-5-amino-7-methyl-1H-pyrrolo[1,2-a]benzimidazole

生成物 1

HCID 102198607-Methyl-2,3-dihydro-1H-pyrrolo[1,2-a] benzimidazole-5,8-dione

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

To a suspension of 218 mg (0.83 mmol) of 25 in 10 mL of water, containing 200 mg of monobasic potassium phosphate, was added a solution of 1.34 g of Fremy's salt in 50 mL of water containing 500 mg of monobasic potassium phosphate. The reaction mixture was stirred at room temperature for 2 hours and extracted with 3×50 mL portions of chloroform. The dried extracts (sodium sulfate) were concentrated and then chromatographed over silica gel, employing chloroform as the eluant, to afford yellow-colored 26, 105 mg (61%) yield. Recrystallization from chloroform/hexane afforded analytically pure 26: mp 162°-164° C.; TLC (methanol chloroform[10:90]), Rf =0.62; IR(KBr pellet) 1675, 1659, 1647, 1515, 1154 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ6.54 (1 H, quartet, J=1.6 Hz, C(6) proton coupled to 7-methyl), 4.16 (2 H, t, J~7 Hz, C(1) methylene), 2.86 (2 H, t, J~7 Hz, C(3) methylene), 2.62 (2 H, quintet, J~7 Hz, C(2) methylene), 2.00 (3 H, d, J=1.6 Hz, 7-methyl coupled to C(6) proton); mass spectrum (EI mode) m/z 202 (P+), 174 (P+ -CO), 146 (P+ -2CO), Anal. Calcd for C11H10N2O2 : C, 65.33; H, 4.98; N, 13.85. Found: C, 65.15; H, 4.70; N, 13.61.

後処理

  1. extractionextracted with 3×50 mL portions of chloroform
  2. concentrationThe dried extracts (sodium sulfate) were concentrated
  3. customchromatographed over silica gel
  4. customto afford yellow-colored 26, 105 mg (61%)
  5. customyield
  6. customRecrystallization from chloroform/hexane
  7. customafforded analytically pure 26

出典と根拠

ORDレコード
ord-f3c60b16a6624fcc932e8046247f075c
出典データセット
uspto-grants-1991_05
特許番号
US05015742

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