Formaldehyde → 1-Acetylethylene dimethyldithiocarbamate

HRID 596492

Reaction equation

HRID 596492 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[S:9])[S:4][CH2:5][C:6]([CH3:8])=[O:7].C=O.[C:13](=S)=S.CN(C)C(=S)[S-].C[NH2+]C>CO>[CH3:1][N:2]([CH3:10])[C:3](=[S:4])[SH:9].[C:6]([CH:5]=[CH2:13])(=[O:7])[CH3:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6348Carbon DisulfideHCID 11728Dimethyldithiocarbamic acid, dimethylamineHCID 29494Carbamodithioic acid, N,N-dimethyl-, 2-oxopropyl ester

Product 1

HCID 867345331-Acetylethylene dimethyldithiocarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetonyl dimethyldithiocarbamate (3.6 grams, 0.020 mole), formaldehyde (1.6 grams of 37% aqueous solution, 0.020 mole), carbon disulfide (0.010 mole, 0.8 gram), and dimethylammonium dimethyldithiocarbamate (3.3 grams, 0.02 mole) in methanol (15 ml.) was stirred and heated at 39° C.-43° C. for 160 minutes. The reaction mixture was then cooled in ice and the precipitated product was filtered off, washed with cold methanol, and dried in air. The yield of product melting at 104° C.-106.5° C. (prior sintering) was 5.2 grams (84%). Repeated recrystallization from methylene chloride-methanol solution without heat gave the analytical sample of 1-acetylethylene dimethyldithiocarbamate melting at 105° C.-107.5° C. (prior sintering). The structure was determined from the infrared spectrum and elemental analysis.

Workup

  1. temperatureheated at 39° C.-43° C. for 160 minutes
  2. temperatureThe reaction mixture was then cooled in ice
  3. filtrationthe precipitated product was filtered off
  4. washwashed with cold methanol
  5. customdried in air
  6. customrecrystallization from methylene chloride-methanol solution
  7. temperaturewithout heat

Sources & evidence

ORD record
ord-dbd5440f824c455d9372c90f81bbecf4
Source dataset
uspto-grants-1977_03
Patent number
US04011230

Linked notes

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