4-Chlorobenzoyl chloride → HCID 21736676, compound

HRID 1834397Notes

Reaction equation

HRID 1834397 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:9]1[CH:10]=[CH:2][CH:3]=[CH:4][C:5]=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 21736676HCID 21736676, 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 hrs. and stirred at room temperature for an additional 10 hrs. 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-o-chlorobenzoyl)-3-ethoxycarbonyl-4-ethyl-1-methylpyrrole-2-acetate as a white solid, m.p. 72°-74° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 10 hrs
  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-35e163c53ef9404e8bcba7a9575d6268
Source dataset
uspto-grants-1978_01
Patent number
US04070368

Reaction notes

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