Methyl iodide → Methyl 4-((1-Methyl-1H-benzimidazol-2-yl)methyl)benzoate

HRID 1163087ノート

反応式

HRID 1163087 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:21][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59468704methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate

生成物 1

HCID 59468706Methyl 4-((1-Methyl-1H-benzimidazol-2-yl)methyl)benzoate収率 28%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

A solution of methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate (0.2 g, 0.75 mmol) in acetone was treated with potassium carbonate (0.31 g, 2.2 mmol), cooled to 0° C., treated dropwise with and methyl iodide (0.070 mL, 1.1 mmol), heated at 40° C. for 12 h, cooled to room temperature, and filtered. The filtrate was evaporated under reduced pressure. Purification of the resultant residue by column chromatography (silica, chloroform) afforded the title product (28%). 1H NMR (400 MHz, CDCl3): 7.98 (d, J=8.4 Hz, 2H), 7.7 (m, 1H), 7.37 (m,5H), 4.38 (s, 2H), 3.9 (s, 3H), 3.5 (s, 3H). [M+H] 281.

後処理

  1. temperatureheated at 40° C. for 12 h
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customPurification of the resultant residue by column chromatography (silica, chloroform)

出典と根拠

ORDレコード
ord-42c45dc29a8646809c544ccce74584c4
出典データセット
uspto-grants-2010_10
特許番号
US07820825B2

反応ノート

読み込み中…