Triethylamine → HCID 84426875, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dansyl chloride (270 mg, 1.00 mmol) in CH2Cl2 (10 mL) was added aminoacetaldehyde dimethyl acetal (130 μL, 1.2 mmol) and Et3N (170 μL, 1.2 mmol); the solution was allowed to stir for 1 h at 25° C. The reaction mixture was then evaporated to dryness under reduced pressure and the material left was purified by silica gel chromatography using a gradient of MeOH (0→1%) in CH2Cl2 as the eluent. Fractions containing the product were collected and evaporated to dryness under low pressure affording 11 (318 mg, 940 μmol) as a solid in a yield of 94%. 1H NMR (300 MHz, DMSO-d6): δ 8.45 (dt, J=8.5, 1.1 Hz, 1H), 8.29 (dt, J=8.8, 0.9 Hz, 1H), 8.16 (t, J=5.5 Hz, 1H), 8.10 (dd, J=7.3, 1.1 Hz, 1H), 7.61 (t, J=8.5 Hz, 1H), 7.58 (t, J=8.5 Hz, 1H), 7.25 (dd, J=7.6, 0.7 Hz, 1H), 4.11 (t, J=5.5 Hz, 1H), 3.06 (s, 6H), 2.89 (t, J=5.5 Hz, 2H), 2.81 (s, 6H). 13C NMR (75 MHz, DMSO-d6): δ 151.2, 136.2, 129.3, 128.9, 127.9, 127.7, 123.5, 119.1, 115.0, 102.4, 53.3, 44.9, 43.9. +ESI-HRMS: Calcd for C16H22N2O4S [M+H]+ 339.1373. found 339.1374.

Provenance & Evidence