Electric Literature of 109903-35-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 109903-35-7 name is 4-Amino-N-methylbenzenemethanesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Example 23: 1-(4-{[5-acetyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)- ylidene]amino}phenyl)-lambda/-methylmethanesulfonamide hydrochloride; A mixture of 4-amino-N-methyl-alpha-toluenesulphonamide (200mg, I .Ommol), ethyl isothiocycanate (104mg, 1.20mmol, 0.1 ml) and triethylamine (0.2ml) in ethanol (5ml) was stirred at reflux for 2 hours. The solvent was then removed by rotary evaporation, the resulting material was then suspended in toluene (5ml) and treated with 3-chloro-2,4- pentanedione (0.14g, 1.05mmol, 0.13ml) and the whole mix stirred at 9O0C (oil bath temperature) for 3 hours, and allowed to cool. The reaction mix was filtered and the filtrate evaporated under reduced pressure to give a yellow oil, which was purified by MDAP (mass directed auto-preparation). The relevant fractions were combined and the solvent removed by rotary evaporation to give a brown oil, which was dissolved in dichloromethane (1 ml) and treated with 1 M ethereal HCI (1 ml). The solvent was removed by air drying. The product was triturated in ether, the liquid was decanted off and the residual material was vacuum oven dried to give the title compound as a beige coloured solid (98mg, 24%).LC/MS (ES): Found 368 (ES+), retention time 2.35mins. Ci6H2IN3O3S2 requires 367. 1 H-NMR (400MHz, MeOD-d4): delta 1.49 (3H, t, J=7Hz), 2.52 (3H, s), 2.71 (3H, s), 2.76 (3H, s), 4.31 (2H, m), 4.42 (2H, s), 7.55 (2H, m), 7.66 (2H, d, J=8Hz).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-methylbenzenemethanesulfonamide, and friends who are interested can also refer to it.
Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53448; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics