Reference of 129378-52-5,Some common heterocyclic compound, 129378-52-5, name is 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, molecular formula is C11H23N3O2SSi, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Intermediate 26: 4(5)-Chloro-1 H-imidazoleHO. alphaTo a solution of 2-[(1 ,1-dimethylethyl)(dimethyl)silyl]-N,N-dimethyl-1 H-imidazole-1- sulfonamide (for preparation see US2005075366,15 g, 51.8 mmol) in dry THF (100 ml_), under nitrogen and at -7O0C, a 1.6M solution of butyllithium in hexane (34.0 ml_, 54.4 mmol) was slowly added. The temperature was allowed to reach -550C in 1 hour then cooled down to -780C and dimethylsulfamoyl chloride (8.33 ml_, 78 mmol) was slowly added and the mixture was stirred at -780C for 30min and at 2O0C for 2 hours. The solvents were removed by evaporation and the residue was stirred with 2M HCI solution (100ml) for 12 hour at room temperature. Complete deprotection of the nitrogen was achieved while partial TBDMS deprotection was observed. The aqueous acid solution was basified with KOH pellets and the aqueous phase was extracted with EtOAc. The organic phases were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was treated with a 1 M solution of TBAF in THF (51.8 ml_, 51.8 mmol) and heated to 6O0C for 2 hours. The volatiles were removed under vacuo and the residue was chromatographed to give the title compound (3.5 g, 34.1 mmol); UPLC/MS Rt=O.33 min; m/z (ES): 103 and 105 [M+H]+; 1H NMR (CDCI3): delta 7.00 (d, 1 H), 7.57 (d, 1 H), 11.54 (brs, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, its application will become more common.
Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
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