1,2-Dichloroethane → HCID 23392185, compound

Participants

Reaction Steps

6-Methoxy-benzo[b]thiophene-3-carboxylic acid (See Titus, R. L.; Titus, C. F. J. Heterocycl. Chem., 1973, 10, 679-681, incorporated herein by references), (1.2 g, 5.77 mmol) was stirred in dry CH2Cl2 (50 mL) with N,O-dimethyl-hydroxylamine hydrochloride (620 mg, 6.35 mmol). HOBT (1.54 g, 8.08 mmol), EDC (1.54 g, 8.08 mmol), and DIEA (2.16 mL, 12.11 mmol) were added, and the reaction stirred 3 h at r.t. The reaction was diluted with CHCl3 (50 mL) and washed with H2O, 1 N HCI, H2O, saturated NaHCO3, and brine (25 mL each). Organics were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (30% to 50% EtOAc/hexanes) gave 952 mg (66%) of 6-methoxy-benzo[b]thiophene-3-carboxylic acid methoxy-methyl amide as a clear oil. 1H NMR (300 MHz, CDCI3) δ8.11 (d, 1H, J=9.0 Hz), 7.89 (s, 1H), 7.31 (d, 1H, J=2.4Hz), 7.06 (dd, 1H, J=9.0, 2.4Hz), 3.88 (s, 3H), 3.61 (s, 3H). 3.40 (s, 3H). Anal. (C12H13NO3S) C, H, N. Calculated C=57.39, H=5.21, N=5.57; found C=57.39, H=5.11, N=5.57.

Provenance & Evidence