Ethanol → Benzyl Diethyldithiocarbamate

HRID 2068460

Reaction equation

HRID 2068460 reaction equation
C(O)C.[CH2:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.O.O.[CH2:15]([N:17]([CH2:21][CH3:22])[C:18](=[S:20])[S-:19])[CH3:16].[Na+]>O>[CH2:15]([N:17]([CH2:21][CH3:22])[C:18](=[S:19])[S:20][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:16]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 7503Benzyl ChlorideHCID 517546Sodium diethyldithiocarbamate trihydrate

Product 1

HCID 590455Benzyl DiethyldithiocarbamateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

More specifically, 10 ml of ethanol solution containing benzyl chloride (4.8 g, 38 mmol, Mw. 126.58) was added dropwise into 50 ml of ethanol solution containing sodium N,N-diethyldithiocarbamate trihydrate (10.3 g, 46 mmol, Mw. 225.31) in nitrogen atmosphere at 0° C. After agitating the reaction solution for 23 hours at room temperature, 150 ml of water was added and extracted by diethylether (200 ml×3 times). The organic layer was washed with water (100 ml×3 times) and was dried by sodium sulfate. Solvent was distilled away under reduced pressure using an evaporator so as to obtain benzyl N,N-diethyldithiocarbamate (colorless liquid). Yield point was 17.6 g (yield: 93%), 1H-NMR: δ7.407 ppm to 7.271 ppm (m, 5H, Ar—H), δ4.540 ppm (s, 2H, Ar—CH2S), δ4.082 ppm to 4.012 ppm (q, 2H, —N—CH2—), δ3.763 ppm to 3.692 ppm (q, 2H, —N—CH2—), δ1.311 to 1.252 ppm (m, 6H, —CH2—CH3).

Workup

  1. extractionextracted by diethylether (200 ml×3 times)
  2. washThe organic layer was washed with water (100 ml×3 times)
  3. dry with materialwas dried by sodium sulfate
  4. distillationSolvent was distilled away under reduced pressure
  5. customan evaporator so as

Sources & evidence

ORD record
ord-ecacbc7fc529422db6b9a6f0cca9eaca
Source dataset
uspto-grants-2012_10
Patent number
US08298817B2

Linked notes

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