1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 15604080, compound

Participants

Reaction Steps

To a solution of 4-bromo-2-methoxy-benzoic acid (159 mg, 0.69 mmol) and 2-phenyl-ethenesulfonic acid amide (108 mg, 0.59 mmol) (which was prepared analogously to example 1-1 steps i) to iii) starting from iodoanisole) in dichloromethane (5 mL) and N,N-dimethylformamide (DMF) (2 mL) is added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI) (170 mg, 0.89 mmol) and 4-(dimethylamino)-pyridine (DMAP) (89 mg, 0.73 mmol) at RT. The mixture was stirred at RT for 20 h, and solvent removed under reduced pressure. The crude reaction mixture is partitioned between water (15 mL) and ethyl acetate (15 mL). The organic phase is separated and washed with aq. 1M HCl (4×10 mL), and the aqueous phases combined and back extracted with ethyl acetate (3×10 mL). The organic phases were combined and washed with water (15 mL), brine (2×10 mL) and dried (sodium sulfate) and concentrated in vacuo. After flash chromatography (CH2Cl2/MeOH 10:1) (E)-2-phenyl-ethenesulfonic acid 4-bromo-2-methoxy-benzoylamide can be isolated as a white solid. Yield 65 mg (24%)

Provenance & Evidence