Sodium Hydroxide → HCID 67399877, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-6-(2,2-dimethylcyclopropyl)benzonitrile (381 mmol, 71 mg) (Example 270a) and sulfamoyl chloride (572 mmol, 66 mg) in DMA (1 mL) was stirred at room temperature. After 1 hour, the reaction mixture was diluted with NaOH (1N, 572 mmol, 572 μL) and water (˜30 mL). The precipitate was filtered off, washed with water (3×5 mL) then dissolved in EtOH (10 mL) and NaOH (1N, 953 μL) was added. The reaction was heated to 80° C. with stirring. After completion the solvent were evaporated and the residue was partitioned between water (20 mL) and ether (5 mL). The aqueus layer was extracted with ether (2×5 mL), then acidified to pH˜3 with 1N HCl. The precipitate was collected, washed with water, dried in vacuo to give the desired product (59 mg, 58%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.610 (m, 1H), 0.63 (s, 3H), 0.89 (m, 1H), 1.20 (s, 3H), 2.48 (m, 1H), 6.88 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 7.21 (br. s, 1H), 7.39 (t, J=8 Hz, 1H), 8.42 (br. s, 1H), 10.74 (s, 1H). MS 266 (MH+).

Provenance & Evidence