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

HRID 1606175Notes

Reaction equation

HRID 1606175 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 mins. before 2.84 g. (0.02 mole) of methyl iodide is added. Stirring is continued for 15 mins. 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 mins
  3. filtrationthe precipitate filtered off
  4. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-160ecd256d194f6097f6809d0d9d27ca
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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