1,1-Dichloroethane → ethyl 5-(4-chlorobenzoyl)-3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 1606166Notes

Reaction equation

HRID 1606166 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-].ClC(Cl)C.[CH3:19][N:20]1[CH:24]=[C:23]([CH3:25])[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]1[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:24]2[N:20]([CH3:19])[C:21]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:23]=2[CH3:25])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 85014-Chlorobenzoyl chlorideHCID 118460Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 118461ethyl 5-(4-chlorobenzoyl)-3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 17.5 g. (0.1 mole) p-chlorobenzoyl chloride and 13.3 g. (0.1 mole) aluminum chloride in 150 ml. of dichloroethane is added rapidly to a solution of 25.3 g. (0.1 mole) of ethyl 1,4 -dimethyl-3ethoxycarbonylpyrrole-2-acetate in 100 ml. of refluxing 1,2-dichloroethane. The solution is refluxed for 3.5 hours and 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 residue product is crystallized from cyclohexane and recrystallized from methanol to give ethyl 5-(p-chlorobenzoyl)-1,4 dimethyl-3-ethoxycarbonylpyrrole-2-acetate as a white solid, m.p. 91°-93°C.

Workup

  1. temperatureThe solution is refluxed for 3.5 hours
  2. customThe organic layer is separated
  3. washthe aqueous layer washed with 1,2-dichloroethane
  4. washThe combined organics are washed successively with water, N,N-dimethylaminopropylamine, dilute HCl and brine
  5. dry with materialThe solution is then dried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue product is crystallized from cyclohexane
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6ae4ee2ae6b243b4ad713db81c436feb
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

Loading…