Sodium Iodide → N-(3-chloro-2-propenyl)-N-cinnamyl-trifluoroacetamide

HRID 261208

Reaktionsgleichung

Reaktionsgleichung von HRID 261208
[CH2:1]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].[Cl:19][CH:20]=[CH:21][CH2:22]Cl.[I-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C.O>[Cl:19][CH:20]=[CH:21][CH2:22][N:10]([CH2:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11](=[O:16])[C:12]([F:14])([F:15])[F:13]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 54071740N-cinnamyltrifluoroacetamide

Produkt 1

HCID 54392800N-(3-chloro-2-propenyl)-N-cinnamyl-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel3×

Versuchsvorschrift

A solution of 250 g of N-cinnamyltrifluoroacetamide in 1 liter of hexamethylphosphoric acid triamide (HMPT) is added dropwise with ice-cooling and stirring under a nitrogen atmosphere, to a suspension of 27 g of sodium hydride in 400 ml of HMPT. After the evolution of gas has ceased, a solution of 130 g of 1,3-dichloropropene and 1 g of sodium iodide in 1 liter of HMPT is added dropwise and the mixture stirred for 16 hours at room temperature. The reaction mixture is then poured on to water and extracted with ether. The ethereal solution is dried over sodium sulphate, evaporated and the oily residue chromatographed on 3.5 kg of silica gel with toluene to yield N-(3-chloro-2-propenyl)-N-cinnamyl-trifluoroacetamide as an oil.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ether
  3. dry with materialThe ethereal solution is dried over sodium sulphate
  4. customevaporated
  5. customthe oily residue chromatographed on 3.5 kg of silica gel with toluene

Quellen und Nachweise

ORD-Eintrag
ord-0fcc59ee2553445e950d5b354a1be8ba
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04164583

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