Methane → HCID 12730473, compound

HRID 2213664Notes

Reaction equation

HRID 2213664 reaction equation
ClS([N:5]=[C:6]=O)(=O)=O.[C:8]([C:11]1[NH:12][CH:13]=[CH:14][CH:15]=1)(=[O:10])[CH3:9].CN(C=O)C.C>C(#N)C.C(OCC)(=O)C>[C:6]([C:14]1[CH:15]=[C:11]([C:8](=[O:10])[CH3:9])[NH:12][CH:13]=1)#[N:5]

Participants

7

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 140792-AcetylpyrroleHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 12730473HCID 12730473, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of chlorosulfonylisocyanate in acetonitrile (25 mL) was added dropwise to a solution of 2-acetylpyrrole (10.9 g, 100 mmol) in acetonitrile (25 mL) at 0° C. The reaction mixture turned from yellow to black and was allowed to stir at ambient temperature for 2.5 h. The reaction mixture was cooled to 0° C. and DMF (10 mL) was added. The resulting reaction mixture was then heated to 50° C. for 10 minutes and then poured onto ice to afford a dark colored product. The product was dissolved in ethyl acetate and treated with activated charcoal and filtered. The ethyl acetate was evaporated to afford a tan-colored product. Recrystallization from ethyl acetate afforded 4-cyano-2-acetylpyrrole (4.5 g) as a tan solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe resulting reaction mixture
  3. temperaturewas then heated to 50° C. for 10 minutes
  4. additionpoured onto ice
  5. customto afford a dark colored product
  6. filtrationfiltered
  7. customThe ethyl acetate was evaporated
  8. customto afford a tan-colored product
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fbbe394f550b415d8868cf07402855e0
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

Loading…