Sodium hydride → 2-Chloro-4-(naphthalen-1-ylthio)pyridine

HRID 910956Notes

Reaction equation

HRID 910956 reaction equation
[C:1]1([SH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1>>[Cl:14][C:15]1[CH:20]=[C:19]([S:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 682591-NaphthalenethiolHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 866347242-Chloro-4-(naphthalen-1-ylthio)pyridineYield 95%

Procedure

Using the method of Example 3, Step A, naphthalen-1-thiol (909 mg, 6.31 mmol), 60% sodium hydride in mineral oil (252 mg, 6.31 mmol), and 2-chloro-4-nitropyridine (1.00 g, 6.31 mmol) were reacted to afford 2-chloro-4-(naphthalen-1-ylthio)pyridine (1.53 g, 95% yield) as an oil. 1H NMR (CDCl3) δ 8.22 (d, 1H), 8.03-8.05 (m, 2H), 7.89-7.96 (m, 2H), 7.54-7.59 (m, 3H), 6.82 (s, 1H), 6.72 (d, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a94d524c652949b89529a13e5d97e7fb
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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