(1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE synthesis
- Product Name:(1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE
- CAS Number:5805-57-2
- Molecular formula:C8H9N3
- Molecular Weight:147.18
Yield: 97.3%
Reaction Conditions:
in toluene at 85 - 95; for 9 h;Solvent;Reagent/catalyst;
Steps:
Method B
General procedure: o-Phenylenediamine (0.54 g, 5 mmol) and required amino acid or anthranilic acid (7 mmol) was added sequentially to 10 ml of toluene in a quickfit flask. The reacting mixture was heated under reflux at carefully controlled temperature of 85 - 95 oC for 9 h under the influence of a magnetic stirrer to obtain coloured solution which was allowed to cool overnight. The crystals formed was filtered and air-dried to afford (1H-benzo[d]imidazol-2-yl)methanamine, 10a in 97.3% yield. Due to high efficiency observed in Method B for the synthesis of 10a,it was therefore adopted as the viable method for the synthesis of the rest of the compounds 10b-i. Synthesis of (1H-benzo[d] imidazol- 2- yl) methanamine, 10aTreatment ofo-phenylenediamine (0.54 g, 5 mmol) with L-glycine (0.53 g, 7 mmol) afforded(1H-benzo[d]imidazol-2-yl)methanamine, 10a.1HNMR (400 MHz, DMSO-d6) δ: 7.95 (s, 1H, NH), 7.82-7.80 (d, J= 8.03 Hz, 2H, Ar-H), 7.17-7.13 (m, 2H, Ar-H), 6.44-6.42 (t, J= 5.78 Hz, 2H, NH2-CH2), 3.55-3.53 (t, J= 5.78 Hz, 2H, CH2-NH2). 13C-NMR (100 MHz, DMSO-d6) δ: 142.6, 139.3, 138.9, 125.3, 125.3, 119.2, 119.2, 41.7 ppm. lmax in nm (log εmax): 236 (1.7782), 290 (1.324), 407 (0.8541). IR (KBr): 3384, 3363 (N-H of NH2, two bands), 3245 (N-H), 3021 (C-H aromatic), 2930 (C-H aliphatic), 1605 (C=C), 1580 (C=N), 741 (Ar-H) cm-1. MS: in m/z (rel. %): 295.04 (2M + 1, 10.5%), 148.01 (MH, 24.5%), 147.03 (M+, 20%), 132.04 (M - NH, 100%), 118.07 (M - CH2=NH, 35.3%), 76.11 (68.3%).
References:
Ajani, Olayinka O.;Aderohunmu, Damilola V.;Olorunshola, Shade J.;Ikpo, Chinwe O.;Olanrewaju, Ifedolapo O. [Oriental Journal of Chemistry,2016,vol. 32,# 1,p. 109 - 120]
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