3-(Dimethylamino)prop-2-enenitrile → 3-(2,3-Dichlorophenacylamino)acrylonitrile

HRID 1194116Notes

Reaction equation

HRID 1194116 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:8])[CH2:6][NH2:7].C[N:15](C)[CH:16]=[CH:17][C:18]#N>C(O)C>[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:8])[CH2:6][NH:7][CH:18]=[CH:17][C:16]#[N:15]

Participants

4

Reactant 2

HCID 974973-(Dimethylamino)prop-2-enenitrileHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 679440943-(2,3-Dichlorophenacylamino)acrylonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.0 g of 2,3-dichlorophenacylamine hydrochloride and 10.0 g of 3-dimethylaminoacrylonitrile are heated for 1 hour under reflux in 300 ml of ethanol. After cooling it to room temperature, the reaction solution is poured into a mixture of ice/dilute hydrochloric acid. After extraction with ethyl acetate, the combined extracts are dried over sodium sulfate, filtered, and the filtrate is concentrated. The oily residue is purified by column chromatography (silica gel: elution with a 4:1 mixture of toluene/ethyl acetate). M.p. 125°-127° C. IR (solid/KBr) in cm-1 : 3380 (NH), 2200 (CN), 1715 (CO) 1625 (C=C). 1H-NMR (DMSOd6) in ppm: 4.09 (d, J=15 Hz, 1H); 4.46 (d, J=7 Hz, 2H); 7.2 (q, 1H); 7.4 (broad s, 1H); 7.45-7.85 (m, 3H). Mass spectrum: molecular peak at 254.

Workup

  1. additionthe reaction solution is poured into a mixture of ice/dilute hydrochloric acid
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialthe combined extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. customThe oily residue is purified by column chromatography (silica gel
  7. washelution
  8. additionwith a 4:1 mixture of toluene/ethyl acetate)

Sources & evidence

ORD record
ord-c4e8cc3781ba4076ace4c232ff00600c
Source dataset
uspto-grants-1989_03
Patent number
US04812580

Reaction notes

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