Reacción #165627

Ecuación de reacción

acenaphthene-5-carboxylic acid

acenaphthene-5-carbonyl chloride

product

3-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Et3N

acenaphthene-5-carbonyl chloride

→

title compound

Rendimiento 22.0%

N-[(2Z)-3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-1,2-dihydroacenaphthylene-5-carboxamide

Rendimiento 22.0%

Disolventes

thionyl chloride

THF

Condiciones de reacción

Procedimiento

The acenaphthene-5-carboxylic acid (Aldrich, 0.29 g, 1.4 mmol) in 5 mL of thionyl chloride was converted to acenaphthene-5-carbonyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and acenaphthene-5-carbonyl chloride in 30 mL THF were processed as in Example 134B to afford the title compound (87 mg, 0.24 mmol, 22% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.28 (d, J=0.7 Hz, 3H), 2.33 (d, J=0.7 Hz, 3H), 3.33 (s, 3H), 3.42 (s, 4H), 3.84 (t, J=5.3 Hz, 2H), 4.51 (t, J=5.3 Hz, 2H), 7.30-7.36 (m, 2H), 7.52 (dd, J=8.6, 7.0 Hz, 1H), 8.43 (d, J=7.5 Hz, 1H), 8.81 (d, J=8.8 Hz, 1H); MS (DCI/NH3) m/z 367 (M+H)+; Anal. calculated for C21H22N2O2S: C, 68.82; H, 6.05; N, 7.64. Found: C, 68.63; H, 5.72; N, 7.40.

Fuente