Morpholine → 4-(1,3-Thiazol-2-yl)morpholine

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>>[N:7]1([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 764302-Bromothiazole

Product 1

HCID 154758374-(1,3-Thiazol-2-yl)morpholineYield 95%

Conditions

Temperature: 100 °C

Procedure

2-Bromothiazole (4.592 g) was added to morpholine (24 ml), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system) to give the title compound as a pale yellow oil (4.531 g, yield; 95%).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe resulting organic layer was washed with water
dry with materialdried (over MgSO4)
customevaporated
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record: ord-ce19671af04d48fe811a37ff46e7b8ac
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06340759B1

Reaction notes

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