Acetyl chloride → HCID 45086221, compound

HRID 855609Notes

Reaction equation

HRID 855609 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]#[N:9].[Al+3].[Cl-].[Cl-].[Cl-].[C:14](Cl)([CH3:16])=[O:15]>ClCCCl>[C:14]([C:6]1[C:2]([CH3:1])=[C:3]([C:8]#[N:9])[NH:4][C:5]=1[CH3:7])(=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 27631653,5-dimethyl-1H-pyrrole-2-carbonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 45086221HCID 45086221, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,5-Dimethyl-1H-pyrrole-2-carbonitrile (1.2 g, 10 mmol) was dissolved in anhydrous 1,2-dichloroethane (15 mL) and AlCl3 (2.93 g, 22 mmol) was added proportion-wise. The reaction vessel was purged with N2 and was cooled in an ice-water bath. AcCl (0.71 mL, 10 mmol) was added dropwise and the mixture was stirred for 1 h with cooling and for a further 3 h at room temperature. The reaction mixture was quenched by careful addition of 2 M aq HCl. The acidity of the mixture was adjusted to approximately pH 6 by addition of NaHCO3. After separation of the organic phase, the aqueous phase was extracted with EtOAc (3×100 mL). The combined organic phases were washed (H2O, then brine), dried (MgSO4), and filtered. The solvent was evaporated to afford of 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carbonitrile (1.42 g, 88%) as a pale tan solid. 1H-NMR (CDCl3) δ: 2.44 (s, 3H, CH3), 2.45 (s, 3H, CH3), 2.54 (s, 3H, CH3), 8.75 (br. s, 1H, NH).

Workup

  1. customThe reaction vessel was purged with N2
  2. temperaturewas cooled in an ice-water bath
  3. customThe reaction mixture was quenched by careful addition of 2 M aq HCl
  4. additionThe acidity of the mixture was adjusted to approximately pH 6 by addition of NaHCO3
  5. customAfter separation of the organic phase
  6. extractionthe aqueous phase was extracted with EtOAc (3×100 mL)
  7. washThe combined organic phases were washed (H2O
  8. dry with materialbrine), dried (MgSO4)
  9. filtrationfiltered
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-652fb6a2aed24defa19289f7a5661f68
Source dataset
uspto-grants-2007_08
Patent number
US07262202B2

Reaction notes

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