Tert-butyl 2,2,2-trichloroethanimidate → HCID 9896063, compound

Participants

Reaction Steps

At ambient temperature, to a stirred suspension of 4-[4-(9-bromo-2, 3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (1.033 g, 1.689 mmol) in EtOAc (16.89 mL) was added a solution of t-butyl 2,2,2-trichloroacetimidate (0.7690 g, 3.379 mmol) in cyclohexane (3.379 mL). After 24 h, the reaction was concentrated in vacuo, suspended in CH2Cl2 (10 mL), filtered through a 1"silica gel pad and eluted with 10% acetone/hexane. The filtrate was concentrated to give 0.778 g (69%) of the title compound as an off white solid, mp 168-172° C. 1H NMR (DMSO-d6) δ 1.57 (s, 12 H), 2.15 (s, 6 H), 2.43 (s, 3 H), 7.18 (s, 2 H), 7.45-7.55 (m, 4 H), 7.65 (t, 1 H), 7.96 (d, 1 H), 8.19 (d, 1 H), 10.75 (s, 1 H). IR (KBr) 3400, 2900, 1680, 1380 and 1140 cm-1. mass spectrum (-ESI) m/z 665/667 (M-H). Anal. Calcd. for C33H31BrO6S2 : C, 59.37; H, 4.68; N, 0.00. Found: C, 59.33; H, 4.44; N, 0.10.

Provenance & Evidence