Pyrroline → 2-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone

HRID 2065827Notes

Reaction equation

HRID 2065827 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

Reactant 2

HCID 94395PyrrolineHCID 547815Methyl isocyanoacetate

Product 1

HCID 575712512-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanoneYield 73%

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

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. washthe organic layer was washed with 10% aqueous citric acid (2×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c727136b7f9347838d7449510bdca911
Source dataset
uspto-grants-2012_10
Patent number
US08288556B2

Reaction notes

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