Carbon Disulfide → 2,4-Dichloro-alpha-(nitromethyl)benzyl dimethyldithiocarbamate

HRID 596498Notes

Reaction equation

HRID 596498 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][N+:6]([O-:8])=[O:7].[CH3:14][N:15]([CH3:19])[C:16](=[S:18])[S-:17].C[NH2+]C.C(=S)=S>CO>[CH3:14][N:15]([CH3:19])[C:16](=[S:17])[S:18][CH:4]([CH2:5][N+:6]([O-:8])=[O:7])[C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 11728Dimethyldithiocarbamic acid, dimethylamineHCID 2558822,4-Dichloronitrostyrene

Product 1

HCID 139566472,4-Dichloro-alpha-(nitromethyl)benzyl dimethyldithiocarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dichloro-β-nitrostyrene (6.6 grams, 0.030 mole) was added to a stirred solution of dimethylammonium dimethyldithiocarbamate (5.1 grams, 0.030 mole) and carbon disulfide (1.8 ml., 0.030 mole) in methanol (30 ml.). The temperature of the resulting reaction was 16°-32° C. After 2 hours at room temperature, the precipitated product was filtered off, washed with cold methanol, and dried in air. Recrystallization without heating was accomplished by dissolving the sample in acetone and then adding absolute ethanol to give 2,4-dichloro-α-(nitromethyl)-benzyl dimethyldithiocarbamate melting at 127° C.-128° C.

Workup

  1. customThe temperature of the resulting reaction
  2. customwas 16°-32° C
  3. filtrationthe precipitated product was filtered off
  4. washwashed with cold methanol
  5. customdried in air
  6. customRecrystallization
  7. temperaturewithout heating
  8. dissolutionby dissolving the sample in acetone
  9. additionadding absolute ethanol

Sources & evidence

ORD record
ord-675bd9d6ed3e4404b1fe5093c5e32abd
Source dataset
uspto-grants-1977_03
Patent number
US04011230

Reaction notes

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