4-Chlorobenzoyl chloride → HCID 86584041, compound

HRID 1585616Notes

Reaction equation

HRID 1585616 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-:11].[Al+3].[Cl-].[Cl-].[CH2:15]([O:17][C:18]([C:20]1[C:24]([CH2:25][CH3:26])=[CH:23][N:22]([CH3:27])[C:21]=1[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:19])[CH3:16]>ClCCCl>[Cl:11][C:3]1[CH:2]=[CH:10][CH:9]=[C:5]([CH:4]=1)[C:6]([C:23]1[N:22]([CH3:27])[C:21]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[C:24]=1[CH2:25][CH3:26])=[O:7]

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18424250HCID 18424250, compound

Product 1

HCID 86584041HCID 86584041, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 13.8 g. (0.0788 mole) of p-chlorobenzoyl chloride and 10.5 g. (0.0788 mole) of aluminum chloride in 120 ml. of 1,2-dichloroethane is added to a refluxing solution of 21.8 g. (0.0788 mole) of ethyl 3-ethoxycarbonyl-4-ethyl-1-methylpyrrole-2-acetate. The mixture is heated under reflux for 10 hours and stirred at room temperature for an additional 10 hours. It is then poured into ice-hydrochloric acid. The organic layer is separated, and the aqueous layer washed with 1,2-dichloroethane. The combined organics are washed successively with water, N,N-dimethylaminopropylamine, dilute HCl and brine. The solution is then dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residual red oily residue crystallizes on standing. It is recrystallized twice from methanol to give ethyl (5-chlorobenzoyl)-3-ethoxycarbonyl-4-ethyl-1-methyl-pyrrole-2-acetate as a white solid, m.p. 72-74° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 10 hours
  3. customThe organic layer is separated
  4. washthe aqueous layer washed with 1,2-dichloroethane
  5. washThe combined organics are washed successively with water, N,N-dimethylaminopropylamine, dilute HCl and brine
  6. dry with materialThe solution is then dried over anhydrous magnesium sulfate
  7. customthe solvent evaporated in vacuo
  8. customThe residual red oily residue crystallizes
  9. customIt is recrystallized twice from methanol

Sources & evidence

ORD record
ord-e65f6a9195f54076a1eca2cfcd0c56db
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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