4-(pyridin-4-ylsulfanyl)aniline synthesis
- Product Name:4-(pyridin-4-ylsulfanyl)aniline
- CAS Number:673-09-6
- Molecular formula:C11H10N2S
- Molecular Weight:202.28
Yield: 78%
Reaction Conditions:
with potassium carbonate in DMF (N,N-dimethyl-formamide) at 80;
Steps:
B
To a solution of 4-aminothiophenol (20.2 g, 156.5 mmol) in anhydrous DMF (200 mL) was added 4-chloropyridine hydrochloride (24.4 g, 161.0 mmol) followed by potassium carbonate (44 g, 318.4 mmol). The reaction mixture was heated at 80° C. overnight, then diluted with ethyl acetate (400 mL) and water (400 mL). The aqueous layer was back-extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with a saturated aqueous NaCl solution (200 mL), dried over anhy MgSO4, and concentrated under reduced pressure. The residue was filtered through a pad of silica with ethyl acetate and the resulting material was triturated with an ethyl ether/hexane solution to afford the desired product (24.7 g, 78%). TLC (50% ethyl acetate/50% hexane) Rf 0.25; 1H-NMR (DMSO-d6) δ 5.67 (bs, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.88 (d, J=6.2 Hz, 2H), 7.19 (d, J=8.4 Hz, 2H), 8.27 (d, J=6.2 Hz, 2H), MS[M+H]+=203.
References:
BAYER CORPORATION US2004/2507, 2004, A1 Location in patent:Page/Page column 12-14
![Pyridine, 4-[(4-nitrophenyl)thio]-](/CAS/20210305/GIF/746630-21-7.gif)
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