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>O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-bromothiazole (356 μL, 4.00 mmol) in morpholine (2.09 mL, 24.0 mmol) was warmed at 100° C. in a sealed tube. After 61 hours, the mixture was cooled to room temperature, diluted with 20 mL of water, and extracted with three 30 mL portions of diethyl ether. The combined organic layers were washed with five 30 mL portions of water, 30 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed over SiO2 (20-100% ethyl acetate in hexanes, gradient) to afford 513 mg (75%) of 4-thiazol-2-yl-morpholine.
Workup
- extractionextracted with three 30 mL portions of diethyl ether
- washThe combined organic layers were washed with five 30 mL portions of water, 30 mL of brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was chromatographed over SiO2 (20-100% ethyl acetate in hexanes, gradient)
Sources & evidence
- ORD record
- ord-5e6803b3a4184742bdd816b014b0bbdb
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658637B2
Reaction notes
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