Oxalic Acid → ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 848046Notes

Reaction equation

HRID 848046 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](C#N)=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)(=O)C(O)=O>CCOCC.C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([C:17]2[N:13]([CH3:12])[C:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][C:16]=2[CH3:18])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 98340514-Chlorobenzoyl cyanide

Product 1

HCID 118463ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetateYield 32.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.65 g (0.01 mole) of p-chlorobenzoylcyanide, 1.81 g (0.01 mole) of ethyl 1,4-dimethylpyrrole-2-acetate and 0.08 g of anhydrous oxalic acid in 4 ml of ether was stored in the dark under nitrogen for four days. The solution was diluted with CH2Cl2. The organic solution was washed with 10 percent NaOH solution, dried (MgSO4), and the solvent evaporated in vacuo. The residue was recrystallized from 1,1,1-trichloroethane to give 1.04 g of ethyl 5-(4-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate, mp 105°-108° C., undepressed by admixture with authentic material.

Workup

  1. customfor four days
  2. washThe organic solution was washed with 10 percent NaOH solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. customThe residue was recrystallized from 1,1,1-trichloroethane

Sources & evidence

ORD record
ord-4d8a73c783df49749b58f76aa11acc1b
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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