Triethylamine → beta-Oxo-alpha-(2,4-dichlorophenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

HRID 236350Notes

Reaction equation

HRID 236350 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][C:9]#[N:10])=[O:7].CCN(CC)CC.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N:26]=[C:27]=[O:28]>C(COC)OC>[O:7]=[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)[CH:8]([C:27](=[O:28])[NH:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[Cl:18])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 757892,4-Dichlorophenyl isocyanateHCID 111943553-oxo-3-(1H-pyrrol-2-yl)propanenitrile

Product 1

HCID 13370095beta-Oxo-alpha-(2,4-dichlorophenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 2.1 g of 2-pyrroloylacetonitrile in 15 ml of glyme and 1.8 g of Et3N is treated with a solution of 3 g of 2,4-dichlorophenyl isocyanate in 15 ml of glyme similarly to the preceding examples. Mildly exothermic reaction results in formation of a thick suspension of crystals. After standing overnight, dilution with dry ether and filtration gives the triethylamine salt of β-oxo-α-(2,4-dichlorophenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile, m.p. 180°-2° dec., in form of the enol structure as represented by formula Ia, wherein Py is 2-pyrrolyl, R is hydrogen and Ph is 2,4-dichlorophenyl.

Workup

  1. customMildly exothermic reaction
  2. customresults in formation of a thick suspension of crystals
  3. filtrationdilution with dry ether and filtration

Sources & evidence

ORD record
ord-533a5e0ebcbe47968056320fdaa0f8d5
Source dataset
uspto-grants-1987_02
Patent number
US04644010

Reaction notes

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