2-Aminothiazole → Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate

HRID 2282213Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].Cl[CH:8]([C:14](=O)[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH3:15][C:14]1[N:6]=[C:2]2[N:3]([C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:5][S:1]2

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,3-thiazol-2-amine (10 g, 100 mmol), ethyl 2-chloro-3-oxobutanoate (16 g, 100 mmol) and ethanol (100 mL) was stirred at 80° C. for 1 day. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→50/50) and washed with diisopropyl ether to give the title compound (5.5 g, 26%) as a colorless solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution
additionwas added to the obtained residue
extractionthe mixture was extracted with ethyl acetate
washThe collected organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationThe insoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→50/50)
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-ddd328b974e24d0ea08517ea009ad4c1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139589B2

Reaction notes

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