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

HRID 1868220Notes

Reaction equation

[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

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a42c9c8e075741bdbb768e1daffdb002
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635697B2

Reaction notes

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