Chemistry of antipernicious anemia factors. III. 5,6-Disubstituted benzimidazoles as products of acid hydrolysis of vitamin B12 was written by Beaven, G. R.;Holiday, E. R.;Johnson, E. A.;Ellis, B.;Mamalis, P.;Petrow, V.;Sturgeon, B.. And the article was included in Journal of Pharmacy and Pharmacology in 1949.Safety of 7-Methyl-1H-benzo[d]imidazole This article mentions the following:
N-(p-Tolylsulfonyl)-nitroanilides are prepared from the nitro amine in pyridine treated portionwise with p-MeC6H4SO2Cl, then heated at 100° for 2 h., acidified, and crystallized Yields are 80-95%. The following 2′-nitro-p-toluenesulfonanilides are prepd: 4′-Me (I), yellow needles from alc., m. 104°; 6′-Me (II), yellow prisms from alc., m. 125°; 3′,4′-di-Me (III), prismatic needles from alc., m. 126-7°; 4′,5′-di-Me (IV), yellow blades from alc., m. 149-50°. The sulfonanilides are methylated by refluxing with Me2SO4 in alk. medium; yields, 80-95%. I yields 2′-nitro-N,4′-dimethyl-p-toluenesulfonanilide, pale yellow prisms, m. 128°. The methylated product from II forms silvery leaflets, m. 139-40°; from III, colorless prisms, m. 137°; from IV, m. 125-7°. Mixtures of the N-methyl-p-toluenesulfonanilides, AcOH, and H2SO4 are heated at 100° for 1-2 h. and poured into ice and the hydrolyzed amine recrystallized from alc.; yield, 60-75%. The corresponding 2-nitroanilines are: N,3,4-tri-Me, scarlet prisms with 0.5 H2O, m. 59-60°; N,4,5-tri-Me, resublimed at 0.05 mm. and 100°, orange-red needles, m. 138°. Preparation of benzimidazoles: Shake the nitro amine in EtOH with H (10% Pd-C catalyst), remove the catalyst, dry the solution under N, dissolve the residue in 4 N HCl, add the appropriate aliphatic acid, reflux in N, precipitate with NH3, and recrystallize; yields, 50-60%. The benzimidazoles prepared are: 1-Me, needles [from light petroleum (V)], m. 64°; 2-Me, needles from H2O, m. 176°; 4-Me, needles from AcOEt-V, m. 140°; 5-Me, needles from AcOEt-V, m. 113°, b0.1 169-72°; 1,2-di-Me, needles from AcOEt-V, m. 109-10°; 1,5-di-Me, needles from AcOEt-V, m. 94°; 1,6-di-Me, needles from V, m. 74-5°; 1,7-di-Me, prismatic needles from AcOEt-V, m. 68-70.5°; 2,4-di-Me, prisms from AcOEt, m. 168-9 °; 2,5-di-Me, leaflets from AcOEt-V, m. 202°; 4,5-di-Me, leaflets from aqueous alc., m. 196-7°; 5,6-di-Me, needles from AcOEt-V, m. 199-200°; 1,2,5-tri-Me, plates from AcOEt, m. 141°; 1,2,6-tri-Me, rods from AcOEt-V, m. 119-20 °; 1,2,7-tri-Me, fine needles from V, m. 146-7°; 1,4,5-tri-Me, white needles from V, m. 95-6°; 2,4,5-tri-Me, needles from aqueous alc., m. 188-90°; 1,5,6-tri-Me, needles from AcOEt-V, m. 142-3°; 2,5,6-tri-Me, needles from aqueous alc., m. 233-4°; 1,2,4,5-tetra-Me, long needles from aqueous alc., m. 144-5°; 1,2,5,6-tetra-Me, pale yellow prisms from AcOEt-V, m. 164°. The methylated benzimidazoles are compared spectroscopically with 3 chem. related components, α, β, and γ, separated from the “285 component” by chromatog. The α- and β-components are identified as 1-substituted 5,6-dimethylbenzimidazoles, and γ is 5,6-dimethylbenzimidazole (VI). Only one VI residue is released from vitamin B12 on acid hydrolysis; the benzimidazole nucleus exists preformed in the vitamin, and components α, β, and γ represent successive stages of degradation of a common precursor. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Safety of 7-Methyl-1H-benzo[d]imidazole).
7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 7-Methyl-1H-benzo[d]imidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem