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

HRID 1021651Notes

Reaction equation

HRID 1021651 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][S-:12].[Na+]>CO>[CH3:11][S:12][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2598065-Chloro-2-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 220361825-(Methylthio)-2-nitropyridineYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 5-chloro-2-nitropyridine (3 g, 18 mmol) in MeOH (20 mL), sodium methanethiolate (1.4 g, 20 mmol) was added at 0° C. and the mixture stirred at 20° C. for 2 hours. The resulting suspension was filtered and washed with water, and dried in vacuum to afford crude 117a as a yellow solid (2 g, 66%) without purification for next step. MS: [M+H]+ 171.

Workup

  1. additionwas added at 0° C.
  2. filtrationThe resulting suspension was filtered
  3. washwashed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-f6988726be9a4197908fd7e4c5cccf8c
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

Loading…