Hydrochloric Acid → 5-(2',4'-Dichlorobenzoyl)-1-methylpyrrole-2-acetonitrile

HRID 1585581Notes

Reaction equation

HRID 1585581 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[CH3:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]#[N:24].Cl>ClCCCl>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:21]1[N:17]([CH3:16])[C:18]([CH2:22][C:23]#[N:24])=[CH:19][CH:20]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 666452,4-Dichlorobenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 184243785-(2',4'-Dichlorobenzoyl)-1-methylpyrrole-2-acetonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of 16.6 g. (0.125 mole) of aluminum chloride in 60 ml. 1,2-dichloroethane is added 26.2 g. (0.125 mole) of 2,4-dichlorobenzoyl chloride. The resulting solution is added slowly to a solution of 15 g. (0.125 mole) of 1-methylpyrrole-2-acetonitrile in 60 ml. 1,2-dichloroethane while cooling externally with an ice bath. After the addition is complete, the mixture is stirred for 40 minutes at room temperature followed by heating at reflux for 3 minutes. It is then poured into ice acidified with dilute hydrochloric acid. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid, and saturated sodium chloride solution. It is then dried over magnesium sulfate and the solvent evaporated. The resulting red oily residue is chromatographed on a column packed with neutral alumina and eluted with benzene and ether. The first compound-bearing fractions upon evaporation yield a white solid, 5-(2',4'-dichlorobenzoyl)-1-methylpyrrole-2-acetonitrile, which is purified by recrystallization from methanol, m.p. 129-130° C. Analysis: Calcd. for C14H10Cl2N2O: N, 9.56%. Found: N, 9.51%.

Workup

  1. additionTo a suspension of 16.6 g
  2. additionThe resulting solution is added slowly to a solution of 15 g
  3. additionAfter the addition
  4. temperatureby heating
  5. temperatureat reflux for 3 minutes
  6. additionIt is then poured into ice
  7. customThe organic phase is separated
  8. washwashed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid, and saturated sodium chloride solution
  9. dry with materialIt is then dried over magnesium sulfate
  10. customthe solvent evaporated
  11. customThe resulting red oily residue is chromatographed on a column
  12. washeluted with benzene and ether
  13. customThe first compound-bearing fractions upon evaporation

Sources & evidence

ORD record
ord-c3ec3fca779b4f23a6d71177ce5987dc
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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