Dimethylformamide → 5-ethyl-2-formyl-1H-pyrrole-3-carbonitrile

HRID 2233853Notes

Reaction equation

HRID 2233853 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH2:11]([C:13]1[NH:17][CH:16]=[C:15]([C:18]#[N:19])[CH:14]=1)[CH3:12].C([O-])(=O)C.[Na+]>ClCCCl>[CH2:11]([C:13]1[NH:17][C:16]([CH:9]=[O:10])=[C:15]([C:18]#[N:19])[CH:14]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 552991665-Ethyl-1H-pyrrole-3-carbonitrile2×

Product 1

HCID 860383665-ethyl-2-formyl-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

POCl3 (3.3 ml, 35.67 mmol) was added to 1,2-dichloroethane (4 ml), then anhydrous DMF (2.75 ml, 35.67 mmol) was added very slowly. The mixture was stirred at room temperature for ˜10 minutes. 5-Ethyl-1H-pyrrole-3-carbonitrile (Intermediate 30, 856 mg, 7.13 mmol) in 1,2-dichloroethane (2 ml) was added dropwise and the mixture was heated at 80° C. for ˜30 minutes. The mixture was cooled to room temperature and sodium acetate (2.5 g/5 ml) was added and the mixture was stirred for 1 h. The brown/black emulsion was extracted with DCM (4×50 ml). The combined organic phase was washed with water (2×50 ml) dried over Na2SO4 and concentrated in vacuo to give the title compound. (819 mg).

Workup

  1. temperaturethe mixture was heated at 80° C. for ˜30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. stirringthe mixture was stirred for 1 h
  4. extractionThe brown/black emulsion was extracted with DCM (4×50 ml)
  5. washThe combined organic phase was washed with water (2×50 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb8b12d1327c4aab84c38f1242e82c09
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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