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Adding a certain compound to certain chemical reactions, such as: 598-55-0, name is Methyl carbamate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 598-55-0, category: amides-buliding-blocks
To a solution of methyl carbamate (20.0 g, 266 mmol) in diethyl ether (300 ml) was added SOCl2 (21.0 mL, 288 mmol) at 0 C, after stirring for 5 min the reaction mixture was allowed to warm to rt and stirred for a further 30 min. A solution of pyridine (40.9 mL, 506 mmol) in diethyl ether (60.0 mL) was added slowly over 1.5 h and then stirred for further 1.5 h. The resulting precipitate was filtered under N2. The filtrate was concentrated in vacuo to give 9 (32.0 g, 264 mmol, Quant.) as yellow oil. The material was used without any further purification [1H NMR (400 MHz, CDCl3) delta 3.94 (3H, s, CH3)]. To a solution of methyl N-(sulfinylidene)carbamate (9, 10.0 g, 83 mmol) in benzene (60.0 mL) was added freshly distilled cyclopentadiene (9.7 mL, 116 mmol) dropwise and the resulting solution was stirred for 20 h at rt. The solution was diluted with THF (110 mL) and phenylmagnesium bromide (1 M in THF, 83.0 mL, 83 mmol) was added over 45 min then stirred for 30 min before being quenched by addition of satd aq NH4Cl (100 mL). Extracted with EtOAc (3 × 100 mL), combined organic phases were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo. Purification (MPLC, Si, EtOAc/petrol, 80%) gave 10 as mixture of diastereomers in approx. 85% purity, which was used in the subsequent reaction (10.4 g, thick oil, estimated 48% yield taking into account small impurities). 4.2.1 Compound 1012b Orange coloured oil. Rf = 0.72 (EtOAc); IR cm-1 3011, 2360, 2341, 1716, 1516; 1H NMR (400 MHz, CDCl3) delta 7.57-7.47 (5H, m, H-Ar), 6.17-5.99 (2H, m, H-2 and H-3), 5.83 (1H, d, J = 8.8 Hz, NH), 4.78 (1H, dd, J = 8.8 and 8.7 Hz, H-1), 3.84-3.78 (1H, m, H-4), 3.68 (3H, s, CH3), 2.17 (1H, ddd, J = 15.3, 8.7 and 8.5 Hz, H-5), 1.78-1.73 (1H, m, H-5); 13C NMR (100 MHz, CDCl3) 171.1 (CO2Me), 156.3 (C-Ar), 142.0 (C-2 or C-3), 130.9 (C-Ar), 129.3 (C-Ar), 129.1 (C-Ar), 128.0 (C-2 or C-3), 124.0 (C-Ar), 71.2 (C-4), 53.4 (C-1), 52.0 (CH3), 29.2 (C-5); HRMS ESI+ m/z C13H15NO3S calculated: 288.0665 [M+Na]+, found: 288.0654
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Reference:
Article; Cully, Sarah J.; Storr, Thomas E.; Rawling, Michael J.; Abeysena, Induka R.; Hamza, Daniel; Jones, Geraint; Pearce, Christopher A.; Quddus, Abdul; Lewis, William; Stockman, Robert A.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5249 – 5257;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics