Pyrroline → 2-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone
Reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].[NH:8]1[CH:12]=[CH:11][CH2:10][CH2:9]1>>[N+:1]([CH2:3][C:4]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)=[O:6])#[C-:2]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
Prepared in accordance with Method B with methyl isocyanoacetate (1.00 g, 10.10 mmol) and dihydro-1H-pyrrole (1.01 mL, 15.15 mmol). The reaction mixture was stirred 5 h at 50° C. and concentrated. The residue was dissolved in dichloromethane (50 mL) and the organic layer was washed with 10% aqueous citric acid (2×25 mL), dried over MgSO4, filtered and evaporated. 2-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone SLA 07178 was obtained (1.0 g, 73% yield) as a yellow solid.
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in dichloromethane (50 mL)
- washthe organic layer was washed with 10% aqueous citric acid (2×25 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a19a316a67c44aa78794d022d6fe270d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927589B2
Reaction notes
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