Potassium Hydroxide → 2-Bromo-6-[(4,6-dimethoxy-2-pyrimidinyl)thio]benzoic acid

HRID 2106967Notes

Reaction equation

HRID 2106967 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([SH:11])[C:7]=1[C:8]([OH:10])=[O:9].[OH-].[K+].CS([C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=1)(=O)=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([S:11][C:18]2[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=2)[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 12423631HCID 12423631, compound

Product 1

HCID 150594242-Bromo-6-[(4,6-dimethoxy-2-pyrimidinyl)thio]benzoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.0 g of 6-bromothiosalicylic acid was dissolved in 20 ml of an aqueous solution of 4.0 g of potassium hydroxide, and then, 6.9 g of 2-methylsulfonyl-4,6-dimethoxypyrimidine and 20 ml of dimethylformamide were added thereto. The mixture was stirred at room temperature for one hour and poured into a large amount of ice water. The aqueous solution was washed with chloroform and then, neutralized with hydrochloric acid. An oily substance thereby released was extracted with diethyl ether. The diethyl ether layer was dried and passed through a FURORIDIL short column. Diethyl ether was distilled off under reduced pressure to obtain 3.9 g of the desired compound as white powder.

Workup

  1. washThe aqueous solution was washed with chloroform
  2. extractionAn oily substance thereby released was extracted with diethyl ether
  3. dry with materialThe diethyl ether layer was dried
  4. distillationDiethyl ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f73cdf7034e646b18316253dd082b57c
Source dataset
uspto-grants-1990_06
Patent number
US04932999

Reaction notes

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