Hydrochloric Acid → 2-[(4,6-Dimethoxypyrimidin-2-yl)thio]-6-methylbenzoic acid

HRID 1650079Notes

Reaction equation

[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16](S(C)(=O)=O)[N:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([S:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=2[C:4]([OH:6])=[O:5])[N:15]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Then, 3.6 g of 2-mercapto-6-methylbenzoic acid, 4.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 3.5 g of unhydrous potassium carbonate were dissolved in 20 ml of dimethylformamide, and then the mixture was stirred at from 110 to 120° C. for one hour. The reaction solution was poured into a large amount of water, and concentrated hydrochloric acid was added thereto. Then, the mixture was extracted with chloroform. The chloroform layer was washed with water and dried, and then the solvent was distilled off under reduced pressure. The crude crystals were purified by column chromatography by using a developing solvent of hexane/ethyl acetate and recrystallized from ethyl acetate to obtain 0.8 g of 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-methylbenzoic acid as white powder. Melting point: 131°-132° C.

Workup

additionwas added
extractionThen, the mixture was extracted with chloroform
washThe chloroform layer was washed with water
customdried
distillationthe solvent was distilled off under reduced pressure
customThe crude crystals were purified by column chromatography
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-f4abf0cb65524ae692f2e69e60bbc2ba
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923501

Reaction notes

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