Formaldehyde → 1-Benzoylethylene dimethyldithiocarbamate

HRID 26134

Reaction equation

HRID 26134 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[S:14])[S:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].C=O.[C:18](=S)=S.CN(C)C(=S)[S-].C[NH2+]C>CO>[CH3:1][N:2]([CH3:15])[C:3](=[S:4])[SH:14].[C:6]([CH:5]=[CH2:18])(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6348Carbon DisulfideHCID 11728Dimethyldithiocarbamic acid, dimethylamineHCID 2381112-Oxo-2-phenylethyl dimethylcarbamodithioate

Product 1

HCID 867345341-Benzoylethylene dimethyldithiocarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of phenacyl dimethyldithiocarbamate (12.0 grams, 0.050 mole), formaldehyde (4.1 grams of 37% aquoeus solution, 0.050 mole), carbon disulfide (1.9 grams, 0.025 mole), and dimethylammonium dimethyldithiocarbamate (8.3 grams, 0.050 mole) in methanol (50 ml.) was stirred and heated at 38° C.-40° C. for 2.5 hours. The reaction mixture was then cooled to 0° C. and the precipitated product was filtered off, washed with cold methanol and dried in air. The yield of product melting at 106° C.-108° C. was 17.6 grams (94%). Repeated recrystallization from methylene chloride-methanol and acetone-2-propanol solution without heat gave pure 1-benzoylethylene dimethyldithiocarbamate melting at 106° C.-109.5° C. The structure was determined from the infrared spectrum and elemental analysis.

Workup

  1. temperatureheated at 38° C.-40° C. for 2.5 hours
  2. filtrationthe precipitated product was filtered off
  3. washwashed with cold methanol
  4. customdried in air
  5. customrecrystallization from methylene chloride-methanol and acetone-2-propanol solution
  6. temperaturewithout heat

Sources & evidence

ORD record
ord-51adce84042b46e594db6bfa0dc19b01
Source dataset
uspto-grants-1979_04
Patent number
US04148795

Linked notes

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