Propargyl bromide → 1-(Prop-2-yn-1-yl)imidazolidin-2-one
Reaction equation
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.[CH2:7]([Li])[CH2:8][CH2:9]C.CCCCCC.BrCC#C.S(=O)(=O)(O)[O-].[K+]>O1CCCC1>[CH2:9]([N:3]1[CH2:2][CH2:1][NH:6][C:4]1=[O:5])[C:8]#[CH:7]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of ethylene urea (592 mg, 6.88 mmol) in tetrahydrofuran (15 mL) was added dropwise butyl lithium/hexane solution (2.7 mL, 13.6 mmol) at 0° C. under nitrogen. Thereto was added 3-bromopropyne (410 mg, 6.88 mmol), and the mixture was stirred at 60° C. for 3 hours. Thereto was added 5% aqueous potassium bisulfate solution, and the mixture was extracted with ethyl acetate, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate/hexane 1/1) to give the titled compound (202 mg, 24%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel chromatography (ethyl acetate/hexane 1/1)
Sources & evidence
- ORD record
- ord-e8b54dab38d047f7b31bfa9daba23259
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825155B2
Reaction notes
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