ChemicalBook CAS DataBase List 4,4'-DIPYRIDYL SULFIDE

4,4'-DIPYRIDYL SULFIDE synthesis

9synthesis methods

Product Name:4,4'-DIPYRIDYL SULFIDE
CAS Number:37968-97-1
Molecular formula:C10H8N2S
Molecular Weight:188.25

4556-23-4 Synthesis

4556-23-4
221 suppliers
$6.00/1g

838-85-7 Synthesis

838-85-7
283 suppliers
$9.00/1g

994-30-9 Synthesis

994-30-9
430 suppliers
$12.00/5g

2524-64-3 Synthesis

2524-64-3
404 suppliers
$14.00/5g

37968-97-1
77 suppliers
$23.00/100mg

Yield:37968-97-1 71.6%

Reaction Conditions:

with dmap;triethylamine in dichloromethane;acetonitrile

Steps:

F.4 EXAMPLE F-4
EXAMPLE F-4 R¹ =1-(triethylsilyloxy)ethyl, R² =methyl, OR⁶ =OH→Cl→SHet, R⁷ =p-methoxybenzyl, Het=4-pyridyl. Alcohol (a) (800 mg; 1.68 millimoles) is esterified with diphenyl chlorophosphate (0.42 ml; 1.2 equivalents), 4-(dimethylamino)pyridine (40 mg; 0.2 equivalents), and triethylamine (0.28 ml; 1.2 equivalents) in dichloromethane (10 ml) at -60° C. for 30 minutes and recovered its silyl with triethylsilyl chloride (0.75 ml; 3.9 equivalents) for 1 hour as in Example B-10 to give starting 2-chloride of (a). To a solution of this 2-chloride of (a) in acetonitrile (10 ml) are added 4-mercaptopyridine (280 mg; 1.5 equivalents) and triethylamine (0.35 ml; 1.5 equivalents). After 1 hour at -20° C., the reaction mixture is diluted with dichloromethane and poured into aqueous sodium hydrogen carbonate. The organic layer is separated, washed with aqueous ammonium chloride and water, dried (MgSO₄), and concentrated in vacuum. The residue is purified by chromatography over silica gel (60 g) using toluene-ethyl acetate (1:2) to give 4-pyridyl sulfide (b) (680 mg). Yield: 71.6%. NMR (EM-390, CDCl₃)δ: 0.52-0.68 (6H, m), 0.85-1.00 (9H, m), 1.15 (3H, d, J=8.7 Hz), 1.23 (3H, d, J=6 Hz), 3.18 (1H, dd, J=6.0 Hz, J=2.2 Hz), 3.09-3.30 (1H, m), 3.46, 4.91 (2H, ABq, J=14.4 Hz), 3.78 (3H s), 4.09 (1H, dd, J=13 Hz, J=2.2 Hz), 4.3-4.1 (1H, m), 5.21 (2H, s), 6.85, 7.30 (4H, ABq, J=9 Hz), 7.06, 8.30 (4H, ABq, J=6 Hz) ppm.

References:

Shionogi & Co., Ltd. US4960879, 1990, A

FullText