Electric Literature of 3314-30-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.
General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-(pyrimidin-2-ylmethyl)-1 ,3-thiazole- 4-carboxamide dihydrochloride (196) (563 mg, 0.94 mmol), 1 H-benzimidazole-2-carbaldehyde (178 mg, 1.22 mmol), DIPEA (0.654 ml, 0.74 mmol) in MeOH (15 ml) at room temperature for 24 h, followed by addition of NaBH4 (53 mg, 1.41 mmol) gave the title compound (224 mg, 54percent) as a white solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.20 (br s, 1 H), 8.80 – 8.74 (m, 3H), 7.50 (br s, 2H), 7.40 (t, J = 4.9 Hz, 1 H), 7.21 – 7.07 (m, 2H), 4.64 (d, J = 5.9 Hz, 2H), 3.98 (s, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.96 (t, J = 6.3 Hz, 2H), 2.76 (br s, 1 H) HPLCMS (Method G): [m/z]: 428.2 [M+H]+
The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazole-2-carbaldehyde. I believe this compound will play a more active role in future production and life.
Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem