Methanol → 2-(Methylthio)-5-nitropyridine

HRID 1523271Notes

Reaction equation

HRID 1523271 reaction equation
CO.[S-2:3].[CH3:4][Na].Cl[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1>O>[CH3:4][S:3][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 783082-Chloro-5-nitropyridineHCID 178477781HCID 178477781, compound

Product 1

HCID 44393132-(Methylthio)-5-nitropyridineYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The methanol solution of methyl sodium sulfide (6 g, 86 mmol) was added portionwise at 0° C. into the methanol solution of 2-chloro-5-nitropyridine (2 g, 13 mmol). Then, the reaction mixture was heated to room temperature and stirred for 14 hours. The reaction mixture was poured into 20 mL water, and extracted with ethyl acetate 20 mL for three times. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The residual was recrystallized in diethyl ether to yield yellow solid 2-(methylthio)-5-nitropyridine (2 g, 12 mmol). 1H-NMR (300 MHz, CDCl3): δ 2.64 (3H, s), 7.28-7.32 (1H, m), 9.24 (1H, dd), 9.26 (1H, d); LC-MS m/z: 171 [M++1]; purity (HPLC)>95%.

Workup

  1. extractionextracted with ethyl acetate 20 mL for three times
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residual was recrystallized in diethyl ether

Sources & evidence

ORD record
ord-13e2a64d09864deb866131fb666d4005
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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