Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C₁₁H₁₅NO₃S

Abstract

CCDC no.: 1510979The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was prepared from benzenesulfinamide according to the literature procedure [5]. In a round bottom flask, benzenesulfinamide 3 (0.40 g, 2.80 mmol) was dissolved in dry THF (12 mL) and cooled to −78°C. After stirring the mixture for 10 min at −78°C, n-butyl lithium (2.80 mL, 7.10 mmol) was added dropwise over 10 min. The mixture was stirred for 10 more minutes at −78°C, followed by rapid addition of di-tert-butyl dicarbonate (0.742 g, 3.40 mmol), stirring was continued for 10 min at −78°C which gradually raised the temperature to RT and stirred overnight at room temperature. A saturated solution of NaHCO 3 was then added and diluted with dichloromethane. The water phase was extracted with dichloromethane, dried over MgSO4, filtered, and concentrated under reduced pressure. Flash chromatography using dichloromethane as eluent yielded the title compound (0.306 g, 45%) as a white solid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.49 (s, 1H), 7.68-7.66 (m, 2H), 7.59-7.56 (m, 3H), 1.44 (s, 9H). 13 C NMR (125 MHz, DMSO-d 6 ) δ ppm 153.40, 143.49, 131.26, 128.97, 124.93, 81.47, 27.75. The title compound (10 mg) was dissolved in acetonitrile in a vial by sonication for 3 min. The vial was covered with parafilm with a tiny outlet to enable evaporate ion. Crystals suitable for X-ray diffraction formed over the period of 5 days. Experimental detailsThe data were scaled and absorption correction performed using SADABS [1]. The structure was solved by direct methods using . All hydrogen atoms were placed in idealised positions and refined in riding models with U iso assigned the values to be 1.2 or 1.5 times those of their parent atoms and the constraint distances of CH ranging from 0.95 Å to 1.00 Å.