[CH3:1][C:2]([S:5](Cl)=[O:6])([CH3:4])[CH3:3].Cl.[NH2:9][C:10]([CH3:14])([CH3:13])[C:11]#[N:12].C(N(C(C)C)C(C)C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([C:10]([NH:9][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([CH3:14])[CH3:13])#[N:12]2-methylpropane-2-sulfinic chloride (1.28 g, 9.12 mmol) was added to a stirring solution of 2-amino-2-methylpropanenitrile hydrochloride (1.0 g, 8.3 mmol) in DCM (21 ml) and N-ethyl-N-isopropylpropan-2-amine (3.04 ml, 17.4 mmol) at rt. DMAP (10 mg, 0.083 mmol) was added and the reaction was allowed to stir 1 h. The mixture was then diluted with dichloromethane and washed with sat NH4Cl aq, and sat NaCl aq. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product N-(2-cyanopropan-2-yl)-2-methylpropane-2-sulfinamide (1.45 g, 7.71 mmol, 93% yield) consistent by LCMS and NMR. LC-MS retention time: 2.15 min; m/z (MH+): 189. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (400 MHz, CHLOROFORM-d) δ 1.76 (s, 3H), 1.69 (s, 3H), 1.24 (s, 9H).
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