Reaktion #1803442

Reaktionsgleichung

Compound 75

3-Methylbenzo[b]thiophene-2-thiol

Crude compound 75

3-Methylbenzo[b]thiophene-2-thiol

sulfur

compound 4

2-Chloro-1-(3,4-dihydro-2H-quinolin-1-yl)ethanone

compound 73

2-(Benzo[b]thiophen-2-ylthio)-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone

compound 72

Benzo[b]thiophene-2-thiol

→

compound 76

Ausbeute 5.0%

1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone

Ausbeute 5.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas done at 40° C. in an attempt
2. 2
   SonstigeThe obtained crude material (75)
3. 3
   Sonstigewas used for the next step without further purification
4. 4
   SonstigeThe product was purified by column chromatography

Vorschrift

Compound 75 was obtained according to the procedure used to synthesize compound 72, except the addition of sulfur was done at 40° C. in an attempt to avoid significant formation of disulfide. The obtained crude material (75) was used for the next step without further purification. 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone (76): Crude compound 75 (0.55 g, 3.0 mmol) was coupled with compound 4 (0.48 g, 2.3 mmol) according to procedure used to synthesize compound 73. The product was purified by column chromatography to yield compound 76 (95 mg, 5% for two steps): MS: m/z+354.1 [M+H]+; Anal. Calcd (found) for C20H19NOS2.0.1H2O: C, 67.61; (67.59), H, 5.45; (5.48), N, 3.94; (3.94), S, 18.05; (17.75).

Quelle