Chlorosuccinimide → HCID 25106870, compound

Participants

Reaction Steps

A room temperature solution of 1 (14 mg, 0.026 mmol) and N-chlorosuccinimide (4 mg, 0.029 mmol) dissolved in N,N-dimethylformamide (1 mL) was stirred for 40 min., after which time HPLC indicated no 1 remained. The reaction was partitioned between ethyl acetate and 10% sodium thiosulfate aqueous solution. The organic separation was washed twice with water then brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a colorless solid. The product was isolated by semi-preparative reversed phase HPLC to afford a colorless solid. LC-MS ESI (neg.) m/z: 567.1 (M−H). 1H NMR (400 MHz) (d6-DMSO) δ 11.41 (s, 1H); 9.66 (br s, 1H); 7.64 (d, J=8 Hz, 1H); 7.52 (s, 1H); 7.18 (d, J=8.0 Hz, 1H); 6.86 (s, 1H); 6.61 (d, J=8.0 Hz, 1H); 6.35 (d, J=8.0 Hz, 1H); 6.23 (d, J=8.0 Hz, 1H); 3.66 (s, 3H); 3.51 (s, 2H); 2.38 (s, 3H) ppm.

Provenance & Evidence