Dimethyl Sulfoxide → ethyl 5-(4-chlorobenzoyl)-alpha,1,4-trimethyl-1H-pyrrole-2-acetate

HRID 1275298Notes

Reaction equation

HRID 1275298 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][C:9]=2[CH3:20])=[O:7])=[CH:4][CH:3]=1.[CH3:23]S(C)=O.[H-].[Na+].CI>O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][C:9]=2[CH3:20])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118463ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 118464ethyl 5-(4-chlorobenzoyl)-alpha,1,4-trimethyl-1H-pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.4 grams (0.02 mole) of ethyl 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate is dissolved in 100 ml. of dimethyl sulfoxide (DMSO) and added to a slurry of 0.48 g. (0.02 mole) of sodium hydride in approximately 30 ml. of DMSO. The mixture is stirred for 30 minutes before 2.84 g. (0.02 mole) of methyl iodide is added. Stirring is continued for 15 minutes. The reaction mixture is then poured into water, and the precipitate filtered off and recrystallized from 2-propanol to yield ethyl 5-(p-chlorobenzoyl)-1,4,α-trimethylpyrrole-2-acetate, m.p. 88-90° C.

Workup

  1. stirringStirring
  2. waitis continued for 15 minutes
  3. filtrationthe precipitate filtered off
  4. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-76e56cda034f4b45a61b3039d562c9f2
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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