Sodium hydride → 2-Chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]pyridine

HRID 910917Notes

Reaction equation

HRID 910917 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[SH:7].[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15]([N+]([O-])=O)[CH:14]=[CH:13][N:12]=1>>[Cl:10][C:11]1[CH:16]=[C:15]([S:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 178480602HCID 178480602, compound

Product 1

HCID 637784912-Chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]pyridineYield 74%

Procedure

Using the method of Example 3, Step A, 1-methyl-1H-imidazole-2-thiol (720 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-(1-methyl-1H-imidazol-2-ylthio)pyridine (1.05 g, 74% yield) as an oil. 1H NMR (CDCl3) δ 8.17 (d, 1H), 7.30 (d, 1H), 7.20 (d, 1H), 6.88 (s, 1H), 6.80 (d, 1H), 3.70 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-81bae191b26b49309793c1d685ffe3a3
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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