1H-BENZIMIDAZOLE, 4-METHOXY- synthesis

5synthesis methods

Product Name:1H-BENZIMIDAZOLE, 4-METHOXY-
CAS Number:27080-53-1
Molecular formula:C8H8N2O
Molecular Weight:148.16

64-18-6 Synthesis

64-18-6
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$22.12/250ML

37466-89-0 Synthesis

37466-89-0
88 suppliers
$30.00/100mg

27080-53-1
34 suppliers
$27.00/250mg

Yield:27080-53-1 83.9%

Reaction Conditions:

for 4 h;Reflux;

Steps:

6.1.4 4-Methoxy-1H-benzo[d]imidazole (3)

The reaction mixture of 3-methoxy-o-phenylenediamine (2, 190mg, 1.37mmol)and HCOOH (5mL) was refluxed for 4h, then cooled to room temperature and poured into ice/ water (20mL). The mixture was treated with 10% NaOH aqueous solution to pH≈8 and then extracted with ethyl ether (15mL×3). The combined extracts were washed with water and brine, then dried over anhydrous MgSO₄. The organic phase was concentrated to give the crude product, which was purified by column chromatography with CH₂Cl₂-MeOH (v/v=60/1). The desired product 4-methoxy-1H-benzo[d]imidazole (162mg) was afforded as white powder with 83.9% yield. M.p. 165-167°C; ¹H NMR (acetone-d₆, 300MHz, δ ppm): 8.08 (1H, s), 7.21 (1H, d, J=7.8Hz), 7.11 (1H, t, J=7.8Hz), 6.73 (1H, d, J=7.8Hz), 3.97 (3H, s); HRMS (ESI): m/z, calcd. For C₈H₉N₂O [M+H]⁺ 149.0709 found 149.0707.

References:

Zhou, Jie;Jin, Jing;Zhang, Yi;Yin, Yuwen;Chen, Xiaoguang;Xu, Bailing [European Journal of Medicinal Chemistry,2013,vol. 68,p. 222 - 232]

37466-89-0 Synthesis

37466-89-0
88 suppliers
$30.00/100mg

64-19-7 Synthesis