4-Chlorobenzoyl chloride → HCID 21411840, compound

HRID 2071683Notes

Reaction equation

HRID 2071683 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[CH:24]=[CH:23][N:22]([CH3:25])[C:21]=1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:19])[CH3:16]>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:23]2[N:22]([CH3:25])[C:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[CH:24]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13316134Ethyl 2-(2-ethoxy-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 21411840HCID 21411840, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 28 ml. (0.22 mole) of p-chlorobenzoyl chloride and 29.4 g. (0.22 mole) of aluminum chloride in 160 ml. of 1,2-dichloroethane (DCE) is added to a refluxing solution of 52.7 g. (0.22 mole) of ethyl 3-ethoxycarbonyl-1-methylpyrrole-2-acetate in 160 ml. of DCE. The mixture is heated under reflux for 41/2 hours, after which it is poured into ice-hydrochloric acid. The mixture is extracted with CHCl3 and the extract is washed successively with dimethyl-amino-n-propylamine solution, dilute hydrochloric acid, and brine, and is dried over magnesium sulfate. Evaporation of the solvent in vacuo and chromotographing the resulting residue on silica gel with a benzene to ether gradient yields the desired product in the first compound-bearing fractions. The solvent is evaporated from these combined fractions, and the resulting residue is recrystallized successively from methylcyclohexane and isopropanol to yield ethyl 5-(p-chlorobenzoyl)-3-ethoxy -carbonyl-1-methylpyrrole-2-acetate as a white solid; m.p. 91°-93° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 41/2 hours
  3. extractionThe mixture is extracted with CHCl3
  4. washthe extract is washed successively with dimethyl-amino-n-propylamine solution, dilute hydrochloric acid, and brine
  5. dry with materialis dried over magnesium sulfate
  6. customEvaporation of the solvent in vacuo and chromotographing the resulting residue on silica gel with a benzene to ether gradient

Sources & evidence

ORD record
ord-8215febb52d14c4ba00cb848b4425560
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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