Sulfuric Acid → 2-[2-(4-Methyl-1H-imidazol-1-yl)ethyl]aniline

HRID 1868220ノート

反応式

HRID 1868220 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15]C(OC(C)(C)C)=O)[CH:6]=1.OS(O)(=O)=O>CO.O1CCOCC1>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 57437090HCID 57437090、化合物

生成物 1

HCID 451167592-[2-(4-Methyl-1H-imidazol-1-yl)ethyl]aniline収率 94.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

2-(4-Methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)amino]-phenyl]ethane (2.555 g) from Step B above was dissolved in methanol (20 mL) and 10% conc. H2SO4 in dioxane (v/v) (40 mL) was added. The solution was stirred at 25° C. for 4 h. The solution was diluted with methanol and BioRad AG® 1-X8 (OH−) resin was added until the pH was basic. The resin was filtered off and washed with methanol. The combined filtrates were evaporated to dryness and the residue was chromatographed on silica gel using 4% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (1.605 g, 94%): ESMS: m/z 202.0 (MH+); δH (CDCl3) 2.20 (3H, s, 4-CH3), 2.90 (2H, dd, 1-CH2), 3.33 (2H, bs, NH2), 4.09 (2H, dd, 2-CH2), 6.60 (1H, s, Im-H5), 6.68 (1H, d, Ar—H6), 6.74 (1H, dd, Ar—H4), 6.92 (1H, d, Ar—H3), 7.08 (1H, dd, Ar—H5) and 7.22 ppm (1H, s, Im-H2); δC (CDCl3) CH3: 13.8; CH2: 33.7, 46.7; CH: 115.2, 116.3, 119.4, 128.2, 130.1, 136.3; C, 122.3, 138.7, 144.5.

後処理

  1. addition(OH−) resin was added until the pH
  2. filtrationThe resin was filtered off
  3. washwashed with methanol
  4. customThe combined filtrates were evaporated to dryness
  5. customthe residue was chromatographed on silica gel using 4% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

出典と根拠

ORDレコード
ord-a42c9c8e075741bdbb768e1daffdb002
出典データセット
uspto-grants-2009_12
特許番号
US07635697B2

反応ノート

読み込み中…