Water → Diethyl-Dithiocarbamic Acid 4-Vinyl-Phenyl Ester

HRID 1644131

Reaktionsgleichung

Reaktionsgleichung von HRID 1644131
O.O.O.[CH2:4]([N:6]([CH2:10][CH3:11])[C:7](=[S:9])[S-:8])[CH3:5].[Na+].[CH:13]([C:15]1[CH:22]=[CH:21][C:18](CCl)=[CH:17][CH:16]=1)=[CH2:14].O>C(O)C>[CH:13]([C:15]1[CH:22]=[CH:21][C:18]([S:9][C:7](=[S:8])[N:6]([CH2:10][CH3:11])[CH2:4][CH3:5])=[CH:17][CH:16]=1)=[CH2:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 74126p-Vinylbenzyl chlorideHCID 517546Sodium diethyldithiocarbamate trihydrate

Produkt 1

HCID 86618657Diethyl-Dithiocarbamic Acid 4-Vinyl-Phenyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of sodium diethyldithiocarbamate trihydrate (3.5 g, 1.55×10−2 mol) in 20 mL of ethanol was added to a flask equipped with a stirrer, dropping funnel and a reflux condenser. To this solution was added a solution of 4-vinylbenzyl chloride (3.0 g, 1.96×10−2 mol) and ethanol (5 mL), dropwise, over a period of 0.5 h at a temperature of 0° C. The resultant solution was stirred at room temperature for 24 h before pouring into a large volume of water and extracting with diethyl ether. The ether phase was washed three times with water, dried over sodium sulphate, before finally removing the diethyl ether by evaporation. The residue was recrystallised three times from methanol, giving a yield of 2.6 grams (83%). 1H NMR (CDCl3) δ7.36 (s, 4H, C6H4), 6.70 (dd, J=11.6 and 17.5 Hz, 1H, CH═CH2), 5.73 (d, J=17.5 Hz, 1H, CH═CH2), 5.24 (d, J=11.5 Hz, 1H, CH═CH2), 4.54 (s, 2H, CH2S), 4.04 (q, J=7.3 Hz, 2H, NCH2), 3.73 (q, J=6.6 Hz, 2H NCH2), 1.19 (t, J=ca. 7.0 Hz, 6H CH2CH3).

Aufarbeitung

  1. customequipped with a stirrer
  2. extractionextracting with diethyl ether
  3. washThe ether phase was washed three times with water
  4. dry with materialdried over sodium sulphate
  5. custombefore finally removing the diethyl ether
  6. customby evaporation
  7. customThe residue was recrystallised three times from methanol
  8. customgiving a yield of 2.6 grams (83%)

Quellen und Nachweise

ORD-Eintrag
ord-f297fdc7f57c4c21a0c000728fa18235
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124188B2

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