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

HRID 57696Notes

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 were dissolved in 170 ml of water and cooled to 5° C. A solution of 1 g (4.90 mmol) of methyl 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxylate in 18 ml of methanol was then added dropwise, and the solution was stirred at RT for 3 h. Most of the methanol was removed, and the remainder was extracted three times with dichloromethane. The combined organic phases were dried with sodium sulfate. Following removal of the solvent and drying of the residue under high vacuum, the solid obtained (824 mg (43% of theory)) was used without further purification.

Workup

customMost of the methanol was removed
extractionthe remainder was extracted three times with dichloromethane
dry with materialThe combined organic phases were dried with sodium sulfate
customremoval of the solvent
customdrying of the residue under high vacuum
customthe solid obtained (824 mg (43% of theory))
customwas used without further purification

Sources & evidence

ORD record: ord-1a1f964c0ff2448eb83d8889582d4fe8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Reaction notes

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