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

HRID 1282365Notes

Reaction equation

HRID 1282365 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-ec9e066b236b40a69cde2ef5e3766223
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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