Hydrochloric Acid → 2-Methoxy-4-methylthio-5-nitrobenzoic acid

HRID 2293528Notes

Reaction equation

HRID 2293528 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:17][CH3:18])[CH:6]=1.Cl>CS(C)=O>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([S:2][CH3:1])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acid

Product 1

HCID 214770482-Methoxy-4-methylthio-5-nitrobenzoic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a stream of argon, 0.45 g of sodium methanethiolate was added to 5 ml of dimethyl sulfoxide at room temperature, and 0.50 g of 4-chloro-5-nitro-2-methoxybenzoic acid was added in small portions, followed by 2 hours of stirring. After completion of the reaction, the reaction solution was poured into 1N hydrochloric acid aqueous solution, and the thus precipitated product of interest was collected by filtration, washed with water and then dried under a reduced pressure to give 0.45 g of 2-methoxy-4-methylthio-5-nitrobenzoic acid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe thus precipitated product of interest was collected by filtration
  3. washwashed with water
  4. customdried under a reduced pressure

Sources & evidence

ORD record
ord-33dc03e16916412ea831c25c046f3ecd
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

Loading…