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

HRID 2389775Notes

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-855fdfbb40b34ac2940f7fe50c4b9013
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

Loading…