4-Methylbenzoyl Chloride → 1-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrile

HRID 1973680Notes

Reaction equation

HRID 1973680 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9].[C:10]1([CH3:19])[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[CH:12][CH:11]=1>ClC1C=CC=CC=1Cl>[CH3:1][N:2]1[C:6]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=2)=[O:17])=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9]

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-

Product 1

HCID 111074051-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrileYield 39%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 30 g. of 1-methylpyrrole-2-acetonitrile and 60 g of p-toluoyl chloride in 200 ml of o-dichlorobenzene is refluxed under nitrogen for 4 hrs. The mixture is concentrated to near dryness, diluted with 250 ml. of methylene chloride, washed successively with an aqueous solution of dimethylaminopropylamine, dilute hydrochloric acid and potassium carbonate solution. Removal of the organic solvent leaves an oily residue which crystallizes in 80 ml of methanol to give 22.2 g (39%) of 1-methyl-5-(p-toluoyl)-pyrrole-2-acetonitrile. The methanol filtrate is concentrated and the residual oil is hydrolyzed to the amide by brief refluxing with aqueous ethanolic NaOH (10%). The separated solid is collected giving 10.1 g (16.4%) of 1-methyl-5-(p-toluoyl)-pyrrole-2-acetamide. Total yield = 55.4%.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with 250 ml
  3. washof methylene chloride, washed successively with an aqueous solution of dimethylaminopropylamine, dilute hydrochloric acid and potassium carbonate solution
  4. customRemoval of the organic solvent
  5. customleaves an oily residue which
  6. customcrystallizes in 80 ml of methanol

Sources & evidence

ORD record
ord-5b3f0cefd64c448190893b9447ce3cfb
Source dataset
uspto-grants-1976_12
Patent number
US03998844

Reaction notes

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