Carbon Disulfide → alpha-(Nitromethyl)benzyl dimethyldithiocarbamate

HRID 259451Notes

Reaction equation

HRID 259451 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](=[S:5])[S-:4].C[NH2+]C.C(=S)=S.[N+:13]([CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:15])=[O:14]>CO>[CH3:1][N:2]([CH3:6])[C:3](=[S:4])[S:5][CH:17]([CH2:16][N+:13]([O-:15])=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 7626Beta-NitrostyreneHCID 11728Dimethyldithiocarbamic acid, dimethylamine

Product 1

HCID 21324598alpha-(Nitromethyl)benzyl dimethyldithiocarbamateYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethylammonium dimethyldithiocarbamate (16.6 grams, 0.10 mole), carbon disulfide (7.6 grams, 0.10 mole), and β-nitrostyrene (14.9 grams, 0.10 mole) were dissolved in methanol (50 ml.). A rapid exothermic reaction ensued and the product precipitated. The reaction temperature was held to 35° C. with ice cooling. After several hours at 25° C., the product was filtered off, washed with methanol, and dried in air. The crude product melted at ca. 103° - 110° C. and weighed 22.9 grams (85%). Recrystallizations from hot methanol and from acetone-2-propanol solution (without heating) gave 13.8 grams of α-(nitromethyl)-benzyl dimethyldithiocarbamate melting at 104° - 108.5° C. (prior sintering). The infrared spectrum was essentially identical to the spectrum of analytically pure material.

Workup

  1. customA rapid exothermic reaction
  2. customthe product precipitated
  3. customwas held to 35° C. with ice cooling
  4. waitAfter several hours at 25° C.
  5. filtrationthe product was filtered off
  6. washwashed with methanol
  7. customdried in air
  8. customRecrystallizations from hot methanol

Sources & evidence

ORD record
ord-9d95e18e0fc24fe7a73b7a950296539b
Source dataset
uspto-grants-1977_07
Patent number
US04038288

Reaction notes

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