Preparation of ο-(n-hexylthio)benzamides and tests for their fungistatic action was written by Ponci, R.;Gialdi, F.;Baruffini, A.. And the article was included in Farmaco, Edizione Scientifica in 1959.Formula: C11H15NO2 This article mentions the following:
Adding to 0.5 mole thiosalicylic acid in 350 cc. EtOH at 60° 1 mole NaOH in 250 cc. water and 0.6 mole n-C6H13Br in 300 cc. EtOH and 1 g. KI in 10 cc. water, heating at 100° 2 hrs. in a steam of N, diluting with 1 l. water, cooling, filtering with a small amount of C, acidifying with dil HCl in the cold, keeping 1 hr. on ice, filtering, and washing with water gave 92% ο-(n-C6H13S)C6H4CO2H (I), m. 96-7° (95% EtOH). Treating 0.2 mole I with 0.5 mole SOCl2 4 hrs. gave the chloride of I, b3 175-8°. Dropping 0.02 mole I chloride in 40 cc. Et2O at 0° into 40 cc. Et2O containing 0.05 mole NH3, keeping some hrs. at room temperature, evaporating to half volume in vacuo, filtering, and washing the solid first with cold. Et2O then with ice water gave I amide, m. 103-4° (95% EtOH). Using BuNH2 in place of NH3 gave the Bu amide (II) of I, m. 49-50° (ligroine). Adding 0.04 mole I chloride in 60 cc. dioxane to 0.08 mole thiourea in 80 cc. dioxane, refluxing 15 min., keeping 1 hr. at room temperature, evaporating in vacuo, and extracting the residue with Et2O gave after washing, drying, and evaporating I thioureide, m. 98-9° (95% EtOH). Using benzylamine and proceeding as for II gave the benzylamide of I, m. 81-2° (EtOH); PhNH2 gave the anilide of I, m. 73-4° (80% EtOH). The β-naphthylamide of I m. 94° (95% EtOH), p-chloroanilide m. 86-7° (EtOH and ligroine), p-methylanilide of I m. 84-5° (AcOH and EtOH). None of the compounds was active against Candida albicans and only I and II were active against Trichophyton mentagrophytes. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Formula: C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Formula: C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics