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.[Li][CH2:8][CH2:9][CH2:10]C.CCCCCC.BrCC#C.OS([O-])(=O)=O.[K+]>C1COCC1>[O:5]=[C:4]1[NH:6][CH2:1][CH2:2][N:3]1[CH2:10][C:9]#[CH:8]Participants
7
Procedure
To a suspension of ethylene urea (2.0 g, 23.2 mmol) in THF (80 mL) was added dropwise 1.47 N n-BuLi in hexane (15.8 mL, 23.2 mmol) at room temperature. 3-Bromopropyne (2.0 mL, 22.4 mmol) was added and the mixture was stirred for 30 min at room temperature then for 2 h at 50° C. Aqueous 5% KHSO4 was added and the mixture was extracted with ethyl acetate. The Organic layers were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 1:1 to 0:1 hexane/ethyl acetate to give the title compound (641 mg, 22%).
Workup
- waitfor 2 h at 50° C
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe Organic layers were dried over MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography with 1:1 to 0:1 hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-1070d8fecd4a4ab48ff5c57ba6d5f193
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576656B1
Reaction notes
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