1-BENZYL-2-CHLOROMETHYL-1H-BENZOIMIDAZOLE synthesis
- Product Name:1-BENZYL-2-CHLOROMETHYL-1H-BENZOIMIDAZOLE
- CAS Number:7192-00-9
- Molecular formula:C15H13ClN2
- Molecular Weight:256.73
5822-13-9
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$29.00/1g
79-11-8
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$27.00/25g
7192-00-9
24 suppliers
$188.00/500mg
Yield:7192-00-9 71.4%
Reaction Conditions:
with hydrogenchloride in water;Reflux;
Steps:
General procedure for the synthesis of 7 and 8
General procedure: A mixture of N-benzylbenzene-1,2-diamine (6)/N-methylbenzene-1,2-diamine (1 mol) and chloroacetic acid (3 mol)was refluxed for 4 h in 45 mL of 4 N HCl and then cooled toroom temperature and adjusted to pH = 7 with ammonia.The crudes were obtained and purification by columnchromatography on silica gel mesh 60-120 eluting withethyl acetate/hexane gave compound 7/8, respectively. 1-benzyl-2-(chloromethyl)-1H-benzimidazole (7) Yield0.90 g, 71.4%; m. p. 146-148 °C; 1H NMR (400MHz, CDCl3): δ 7.74 (d, 1H, J = 6.48 Hz, Ar-H), 7.27 (m, 6H,Ar-H), 7.05 (dd, 1H, J = 1.48, 4.32 Hz, Ar-H), 5.44 (s, 2H,benzylic), 4.69 (s, 2H, -CH2-Cl); 13C-NMR (100MHz,CDCl3): δ 164.66 (C-1), 129.12 (2C, C-3a and C-7a),128.21 (C1′), 126.39 (C-2′ and C-6′), 123.94 (2C, C-3′ andC-5′), 122.87 (C-4′), 120.40 (2C, C-5 and C-6), 110.14 (2C,C-4 and C-7), 47.19 (C, benzylic), 37.01 (-CH2-Cl); FTIR(neat, cm-1) νmax: 3024 and 3006 (C-H, aromatic), 2976and 2926 (C-H, aliphatic), 736 (C-Cl); GC-MS (m/z) =256 [M]+; anal. calcd. (%) for C15H13ClN2: C, 70.18;H, 5.10; N, 13.81. Found: C, 71.12; H, 5.33; N, 13.25.
References:
Singh, Gagandeep;Singh, Amanjot;Singh, Varinder;Verma, Raman K.;Tomar, Jyoti;Mall, Rajiv [Medicinal Chemistry Research,2020,vol. 29,# 10,p. 1846 - 1866]
4857-04-9
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100-44-7
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$13.50/250G
7192-00-9
24 suppliers
$188.00/500mg
6646-70-4
22 suppliers
$45.00/25mg
7192-00-9
24 suppliers
$188.00/500mg
95-54-5
540 suppliers
$9.00/1g
7192-00-9
24 suppliers
$188.00/500mg
5822-13-9
66 suppliers
$29.00/1g
105-39-5
425 suppliers
$10.00/5g
7192-00-9
24 suppliers
$188.00/500mg