Phosphorus oxychloride → 3-(1-(2-Acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2-propenaldehyde

HRID 1089433Notes

Reaction equation

HRID 1089433 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].CN(C)[CH:16]=[CH:17][CH:18]=[O:19].P(Cl)(Cl)(Cl)=O.C([O-])(=O)C.[Na+]>ClCCCl.O>[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:8]([CH3:13])=[CH:9][C:10]([CH:16]=[CH:17][CH:18]=[O:19])=[C:11]1[CH3:12])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 517045Sodium AcetateHCID 13770049N-(2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl)acetamide

Product 1

HCID 543427433-(1-(2-Acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2-propenaldehyde

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

16.2 g (0.09 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole and 10 g (0.1 mol) of 3-dimethylaminoacrolein are dissolved in 80 ml of 1,2-dichloroethane. 9 ml (0.098 mol) of phosphorus oxychloride are added dropwise at -10° C. After 20 minutes, 41 g (0.5 mol) of sodium acetate in 150 ml of water are added, the mixture is stirred at room temperature for 18 hours and heated at 70° C. for 2 hours, the phases are separated, the organic phase is chromatographed over a silica gel column and the product is recrystallized from isopropanol.

Workup

  1. temperatureheated at 70° C. for 2 hours
  2. customthe phases are separated
  3. customthe organic phase is chromatographed over a silica gel column
  4. customthe product is recrystallized from isopropanol

Sources & evidence

ORD record
ord-0bdc87bd037f4ed58830cf630620aaba
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

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