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

HRID 2400230

Reaktionsgleichung

Reaktionsgleichung von HRID 2400230
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-b11fbe60f5c048cd843060f2395c5889
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08795782B2

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