2-Mercaptobenzoic Acid → 2-(3,5-Dimethoxyphenylthio)benzoic acid

HRID 1533481Notes

Reaction equation

HRID 1533481 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].Cl[C:12]1[CH:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu].[Cu]I>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH:13]=[C:14]([O:20][CH3:21])[CH:15]=1

Participants

7

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 815021-Chloro-3,5-dimethoxybenzene

Product 1

HCID 110335902-(3,5-Dimethoxyphenylthio)benzoic acidYield 10%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of thiosalicylic acid (44 g), 5-chloro-1,3-dimethoxybenzene (49.2 g), potassium carbonate (78 g), copper (powder) (4.3 g) and copper(I) iodide (4.3 g) in N-methyl-2-pyrrolidone (390 ml) was stirred at 190° C. for 10 hours. The reaction mixture was treated by the same procedure as in Example 1 to give 8.0 g (10%) of a compound of the indicated formula (10).

Workup

  1. additionThe reaction mixture was treated by the same procedure as in Example 1

Sources & evidence

ORD record
ord-6563f985266e4c34a0877745579864e9
Source dataset
uspto-grants-2001_03
Patent number
US06207837B1

Reaction notes

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