Water → HCID 86704408, compound

Participants

Reaction Steps

A cold (−78° C.) solution of oxalyl chloride (0.58 mL, 6.7 mmol) in dichloromethane (13 mL) was treated with the dropwise addition of DMSO (0.74 mL) in dichloromethane (4 mL). After 2 minutes, I-13C (684 mg, 6.10 mmol) in dichloromethane (8 mL) was introduced. After 15 minutes, triethylamine (4.25 mL) was introduced dropwise. The reaction was then warmed to room temperature and diluted with dichloromethane and water. The organic phase was collected and washed with 1N HCl (aq.), water, saturated Na2CO3 (aq.), water, and brine. The organic phase was dried (MgSO4), filtered, and concentrated. The crude material was taken upon in ethanol (10 mL) and treated with 50% hydroxylamine (0.56 mL). After overnight stirring, the reaction was concentrated in vacuo. This residue was diluted with DMF (3.5 mL) and cooled to 0° C. NCS (0.91 g, 6.8 mmol) was introduced and the reaction slowly warmed to room temperature and stirred for 2 hours. The reaction was treated with saturated NaCl (aq.) and extracted with Et2O. Organics were washed with brine and then dried (MgSO4), filtered, and concentrated. MS m/z 160.1 (M+1).

Provenance & Evidence