Hydrochloric Acid → 6-(Methylthio)nicotinic acid

HRID 1042628

Reaction equation

HRID 1042628 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][S-:12].[Na+].Cl>CS(C)=O.C(OCC)(=O)C>[CH3:11][S:12][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2428196-Fluoronicotinic AcidHCID 4378561Sodium methanethiolate

Product 1

HCID 8194096-(Methylthio)nicotinic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-fluoronicotinic acid (0.995 g, 7.05 mmol) in 14 mL of DMSO was added sodium thiomethoxide (1.24 g, 17.6 mmol). The mixture was heated 80° C. for 1 h, cooled to rt, and treated with concentrated hydrochloric acid (4.5 mL, 0.054 mol). After 15 min, the mixture was diluted with ethyl acetate and concentrated in vacuo to provide 6-(methylthio)nicotinic acid that gave a mass ion (ES+) of 170.1 for [M+H]+.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62c081f5a656428bb63f3e2ecc0ea5f9
Source dataset
uspto-grants-2013_10
Patent number
US08557992B2

Linked notes

Loading…