Acetic Anhydride → 3-Acetyl-1-(2-acetylaminoethyl)-2,5-dimethylpyrrole

HRID 1089435Notes

Reaction equation

HRID 1089435 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]1[CH3:13])(=[O:3])[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].COCCOC>CCOCC.[Cl-].[Zn+2].[Cl-]>[C:14]([C:10]1[CH:9]=[C:8]([CH3:13])[N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:11]=1[CH3:12])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 80711,2-DimethoxyethaneHCID 13770049N-(2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl)acetamide

Product 1

HCID 145367523-Acetyl-1-(2-acetylaminoethyl)-2,5-dimethylpyrrole

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

13.7 g (0.1 mol) of anhydrous zinc chloride are dissolved in 100 ml of ether and the solution is added to 18.0 g (0.1 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole and 9.5 ml (0.1 mol) of acetic anhydride in 50 ml of ether. After 1 hour at room temperature, 50 ml of ethylene glycol dimethyl ether are added and stirring is continued for 20 hours. After the hydrolysis, the organic phase is concentrated, the residue is chromatographed and the product is recrystallized from ethyl acetate.

Workup

  1. waitis continued for 20 hours
  2. customAfter the hydrolysis
  3. concentrationthe organic phase is concentrated
  4. customthe residue is chromatographed
  5. customthe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-59c3126467824be7ae7abe85ece5af9a
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

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