Sodium hydride → HCID 63778674, compound

HRID 910980Notes

Reaction equation

HRID 910980 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10])(C)C.[H-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18]([N+]([O-])=O)[CH:17]=[CH:16][N:15]=1>>[Cl:13][C:14]1[CH:19]=[C:18]([S:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH3:1])[CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 63778674HCID 63778674, compoundYield 101.7%

Procedure

Using the method of Example 3, Step A, 2-isopropylbenzenethiol (0.749 g, 4.92 mmol), 60% sodium hydride in mineral oil (197 mg, 4.92 mmol), and 2-chloro-4-nitropyridine (0.780 g, 12.6 mmol) to provide 2-chloro-4-(o-tolylthio)pyridine (1.18 g, 91% yield) as an oil. 1H NMR (CDCl3) δ 8.08 (d, 1H), 7.46-7.55 (m, 3H), 7.28 (t, 1H), 6.82 (s, 1H), 6.77 (d, 1H), 3.42 (heptet, 1H), 1.19 (d, 6H).

Sources & evidence

ORD record
ord-3c0aec750c05484f9f1b9dec0902741a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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