2-((1H-benzo[d]imidazol-2-yl)thio)-N-phenylacetamide synthesis
- Product Name:2-((1H-benzo[d]imidazol-2-yl)thio)-N-phenylacetamide
- CAS Number:30065-33-9
- Molecular formula:C15H13N3OS
- Molecular Weight:283.35
Yield:30065-33-9 13 %
Reaction Conditions:
with potassium carbonate in acetone at 60;
Steps:
4.1.2.1 Synthesis procedure for the compounds A1-A17
General procedure: Starting reagents 1,3-dihydro-2H-benzo[d]imidazole-2-thione, 1-15 and 16-17 were synthesized according to the literatures [34-36], respectively. Then, 1,3-dihydro-2H-benzo[d]imidazole-2-thione (1 eq.) was reacted with 1-17 derivatives (1 eq.) in the presence of K2CO3 (1 eq.) in acetone at 60°C for 1.5h. Then, the solution was cooled to the room temperature and cold water was added until precipitation completed. Precipitate was filtered and washed with cold water and dried [14]. The crude product was crystallized from acetonitrile or methanol. 4.1.2.1.1 2-[(1H-Benzo[d]imidazole-2-yl)thio]-N-phenylacetamide (A1) (0027) White solid, yield: 13%; m.p. (MeCN): 203°C (lit. 202.5-204.5°C [37]). 1H NMR (DMSO-d6, 400MHz): δ 4.26 (2H, s), δ 7.05 (1H, t, J=7.4Hz), 7.12-7.16 (2H, m), 7.31 (2H, t, J=7.9Hz), 7.45 (2H, brs), 7.56-7.59 (2H, m), 10.49 (1H, s), 12.63 (1H, s) ppm. 13C NMR (DMSO-d6, 100MHz): δ 36.2, 119.4, 121.5, 123.5, 128.8, 138.8, 149.8, 166.1ppm. IR νmax (cm-1): 3266, 1675, 1527. MS (APCI) m/z: 284.3 [M+H]+. Anal. Calcd for C15H13N3OS.H2O: C: 59.78; H: 5.02; N: 13.94; S: 10.64. Found: C: 60.18; H: 4.90; N: 13.69; S: 10.37.
References:
Saylam, Merve;Ayd?n K?se, Fadime;Pabuccuoglu, Aysun;Barut Celepci, Duygu;Aygün, Muhittin;Pabuccuoglu, Varol [European Journal of Medicinal Chemistry,2023,vol. 248,art. no. 115083]
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