Water → 4-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazole

HRID 1024042ノート

反応式

HRID 1024042 の反応式
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866841377-Bromo-5-chloro-1H-benzimidazole

生成物 1

HCID 866841384-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazole収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 109c (3.5 g, 15 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.14 g, 30 mmol) and iodomethane (1.4 mL, 22.7 mmol). The reaction was stirred at room temperature for overnight. Water (50 mL) was added to quench the reaction and the resulting mixture was extracted with ethyl acetate (5 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (from 4:1 to 1:2) to afford 109d as a white solid (1.4 g, 38%). LCMS: [M+H]+ 245/247. 1H NMR (500 MHz, CDCl3) δ 7.89 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 3.81 (s, 3H).

後処理

  1. customto quench
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate (5 mL×3)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with petroleum ether/ethyl acetate (from 4:1 to 1:2)

出典と根拠

ORDレコード
ord-553315657c694829a329b6c4009c7049
出典データセット
uspto-grants-2014_05
特許番号
US08722676B2

反応ノート

読み込み中…