2-Chloro-5-nitropyridine → 2-(Methylthio)-5-nitropyridine

HRID 2367688Notes

Reaction equation

HRID 2367688 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1>C1COCC1.O>[CH3:1][S:2][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 44393132-(Methylthio)-5-nitropyridineYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium thiomethoxide in THF (53 mL) and H2O (20 mL) cooled to 0° C. was added 2-chloro-5-nitropyridine (LXV) (5.09 g, 32.09 mmol). The reaction was warmed to room temperature and stirred for 2 hrs. The reaction was poured into ice water and stirred for 10 minutes, filtered, washed with water, dried under vacuum to yield 2-(methylthio)-5-nitropyridine (CVII) as a yellow solid (5.14 g, 30.20 mmol, 94.1%). 1H NMR (DMSO-d6) δ ppm 2.62 (s, 3H), 7.57 (d, J=8.9 Hz, 1H), 8.38 (d, J=8.9 Hz, 1H), 9.22 (d, J=2.7 Hz, 1H); ESIMS found for C6H6N2O2S m/z 171.1 (M+H).

Workup

  1. stirringstirred for 10 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-609753d10586425eb1286d5ebd8c0e9d
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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