Methanol → Methyl 4-amino-2-(methylsulfonyl)thiazole-5-carboxylate

HRID 2171513Notes

Reaction equation

O[O:2][S:3]([O-:5])=O.[K+].[NH2:7][C:8]1[N:9]=[C:10](SC)[S:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:19]O>O>[NH2:7][C:8]1[N:9]=[C:10]([S:3]([CH3:19])(=[O:5])=[O:2])[S:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

Conditions

Temperature: 5 °C

Procedure

5.12 g (8.32 mmol) of Oxone® are dissolved in 170 ml of water and cooled to 5° C. A solution of 1 g (4.90 mmol) of methyl 4-amino-2-(methylsulphanyl)-1,3-thiazole-5-carboxylate in 18 ml of methanol is then added dropwise, and the solution is stirred at RT for 3 h. The major amount of methanol is removed and extracted three times with dichloromethane. The combined organic phases are dried with sodium sulphate. After removal of the solvent and drying of the residue under high vacuum, the resulting solid (824 mg (43% of theory)) is employed without further purification.

Workup

customThe major amount of methanol is removed
extractionextracted three times with dichloromethane
dry with materialThe combined organic phases are dried with sodium sulphate
customAfter removal of the solvent
customdrying of the residue under high vacuum
customthe resulting solid (824 mg (43% of theory)) is employed without further purification

Sources & evidence

ORD record: ord-abe1c416d5d84f9bac9122c336f5bad7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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