Shepherd, Robert G. published the artcile< Sulfonamide preparations in glacial acetic acid>, Application In Synthesis of 112-63-0, the main research area is ACID/acetic; SULFONAMIDES/preparation.
Because in the preparation of N1-(halophenyl)-N4-acetylsulfanilamides (I) in pyridine or PhNMe2 side reactions take place, the use of AcOH as reaction medium was tried and was found to be satisfactory. In general, 1 mol. aniline in 400-1000 cc. glacial AcOH is heated at 100æ?and treated with a 25% excess of the appropriate sulfonyl chloride. With some anilines the amine-HCl seps. and dissolves on addition of NaOAc. The latter is added in 0.5, 0.25, 0.125, and 0.125 mol. portions with an addnl. 0.25 mol. After each addition the mixture is brought to a boil, H2O is added with stirring, and the clear mixture cooled, causing the separation of I. The following p-AcHNC6H4SO2NHC6H2RR’R” are prepared with the following substituents on the N1-Ph residue: none, 90%, m. 214-15æ? 3,5-di-Cl 87%, m. 239-40æ? 3,5-di-Br, 83%, m. 242-3æ? 3,4,5-tri-Cl, 85%, m. 272-3æ? 2-OMe, 84%, m. 212-13æ? 3-OMe, 68%, m. 192-3æ? 4-OMe, 90%, m. 200-1æ? 3-NO2, 74%, m. 244-5æ? 4-NO2, 56%, m. 263-4æ? 4-NHAc, 50%, m. 293-4æ? Also prepared were: p-O2NC6H4SO2NHC6H3Br2-3,5, 92%, m. 175-6æ? PhSO2NHPh, 89%, m.1 12-13æ? PhSO2NHC6H4Cl-p, 91%, m. 122-3æ? PhSO2NHC6H3Br2-3,5, 77%, m. 130-1æ? In addition to these compounds, 0.2-0.5% PhNHAc is usually formed. For a study of side-reactions, 3.9 g. AcHNC6H4SO2Cl in 10 cc. hot AcOH containing 0.3 g. H2O is treated with 2.7 g. AcONa, causing the separation of 3.6 g. precipitate which on hydrolysis gives 99% PhNH2. When a mixture of 17.7 g. PhSO2Cl (II) and 4.5 g. (CO2H)2 is heated to 200æ?and the volatile material distilled off in vacuo, 46% (PhSO2)2O, m. 92æ? is obtained. PhSO2Cl and AcONa at 230æ?give a distillate containing AcCl, Ac2O, and AcOH with PhSO3Na and unchanged II as residue. When 9.3 g. PhNH2 and 17.7 g. PhSO3Et in 50 cc. AcOH are heated at 90æ?0.5 h., and the mixture is diluted with N HCl and extracted with ether, 1% PhSO2NHPh, m. 114æ? is obtained. The aqueous solution is made alk., extracted with ether, and the ether residue treated with p-MeC6H4SO2Cl, giving N-(p-tolylsulfonyl)-N-ethylaniline, m. 88æ? Bromination of 224 g. p-O2NC6H4NH2 in 2 l. AcOH at 65æ?by addition of 520 g. Br in 1200 cc. AcOH over a period of 4 h. gives 95% 2,6-dibromo-4-nitroaniline (III), m. 204-6æ? III is diazotized with ONSO3H according to Hodgson and Walker (C.A. 28, 1325.9) and deaminated according to H. and Turner (C.A. 37, 1421.3), giving 70% 3,5-Br2C6H3NO2 (IV), m. 106æ? Catalytic reduction of IV with Raney Ni in absolute EtOH at room temperature and atm. pressure gives 80% 3,5-Br2C6H3NH2, m. 56-7æ? with SnCl2 the yield is 64% and with Na2S2O4 only 25%. 3,4,5-Cl3C6H2NH2 is prepared in 70% yield by converting 2,6,4-Cl2(O2N)C6H2NH2 into 3,4,5-Cl3C6H2NO2 according to H. and W., followed by reduction with Raney Ni.
Journal of Organic Chemistry published new progress about Reduction. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Application In Synthesis of 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics