Sodium hydride → HCID 63778830, compound

HRID 910936Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17]([N+]([O-])=O)[CH:16]=[CH:15][N:14]=1>>[Cl:12][C:13]1[CH:18]=[C:17]([S:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:16]=[CH:15][N:14]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 849893-Methoxybenzenethiol

HCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 63778830HCID 63778830, compoundYield 95.1%

Procedure

Using the method of Example 3, Step A, 3-methoxybenzenethiol (884 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 provide 2-chloro-4-(3-methoxyphenylthio)pyridine (1.51 g, 95% yield) as an oil. 1H NMR (CDCl3) δ 8.12 (d, 1H), 7.39 (t, 1H), 7.13 (d, 1H), 7.08 (s, 1H), 7.03 (d, 1H), 6.93 (s, 1H), 6.88 (d, 1H), 3.83 (s, 3H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-2ee9239f9f1d4774a431794190527368
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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