Phosgeniminium chloride → HCID 59770949, compound

Participants

Reaction Steps

A mixture of Tert-butylN—(3-amino-5-bromo-4-hydroxybenzyl)carbamate (300 mg, 0.95 mmol) and dichloromethylenedimethylammonium chloride (phosgene iminium chloride, 240 mg, 1.48 mmol) in 10 mL of dry CH2Cl2 was refluxed for 6 h. After cooling the solution was extracted with EtOAc, washed with NaHCO3, brine and dried (MgSO4). After purification by column chromatography (1% MeOH in CH2Cl2) 192 mg (55%) of the title compound were obtained. 1H NMR (CDCl3) δ 7.14 (s, 1H, H-6); 7.04 (s, 1H, H-4); 5.11 (bs, 1H, NH); 4.31 (d, 2H, J=5.6 Hz, CH2); 3.23, 3.22 (s, 6H, NCH3 2×); 1.48 (s, 9H, (CH3)3C); 13C NMR (CDCl3) δ 163.3 (C-2), 156.2 (CO), 146.6 (C-7a), 145.1 (C-3a), 137.0 (C-5), 122.8 (C-6), 114.3 (C-4), 100.6 (C-7), 79.9 ((CH3)3C), 44.7 (CH2), 38.1 (NCH3×2), 28.8 ((CH3) 3C).

Provenance & Evidence