4-Chlorobenzoyl chloride → HCID 18424370, compound

HRID 863646Notes

Reaction equation

HRID 863646 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[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:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:23]2[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]=2[CH2:25][CH3:26])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 18424370HCID 18424370, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 13.8 g. (0.0788 mole) of ρ-chlorobenzoyl chloride and 10.5 g. (0.0788 mole) of aluminum chloride in 120 ml. of 1,2-dichloroethane is added to a refluxing soluton of 21.8 (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 colution is then dried over anhydrous magnesium solfate and the solven evaporated in vacuo. The residual red oil residue crystallized on standing. It is recrystallized twice from methanol to give ethyl (5-ρ-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 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 colution is then dried over anhydrous magnesium solfate
  7. customthe solven evaporated in vacuo
  8. customThe residual red oil residue crystallized
  9. customIt is recrystallized twice from methanol

Sources & evidence

ORD record
ord-272beef6ce524fa9af16008ffec8ebb8
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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