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

HRID 1868220노트

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HRID 1868220 반응식
[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

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 57437090HCID 57437090, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a42c9c8e075741bdbb768e1daffdb002
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635697B2

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