4-Methyloxybenzyl chloride → HCID 59702062, compound

Participants

Reaction Conditions

Reaction Steps

4-Methoxybenzyl chloride (22.8 mL, 167.42 mmol) was added to a solution of methyl-3-amino-thiophene-2-carboxylate (17.55 g, 111 mmol) in dry CH2Cl2 (20 mL). The solution was mixed well. Excess CH2Cl2 was evaporated and the mixture was heated overnight at 85° C. under vacuum (3 torr). The mixture was cooled to room temperature. Hexane was added to the mixture, which was refluxed for 30 min, and cooled to 0° C. The solids formed were filtered, washed by hexane, and dried to yield 28.19 g (91%) of 3-(4-methoxybenzylamino)-thiophene-2-carboxylic acid methyl ester as red solids. 1H NMR (400 MHz, DMSO-d6) δ 3.71 (s, 6H), 4.42 (s, 2H), 6.77 (d, J=5.6 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 7.25 (d, J=8.8 Hz, 2H), 7.63 (d, J=5.6 Hz, 1H), ppm; MS m/z=278 amu (M++1).

Provenance & Evidence