Formaldehyde → 2-Nitrobutyl dimethyldithiocarbamate

Nitropropane (17.8 grams, 0.20 mole), formaldehyde (16.2 grams of 37% aqueous solution, 0.20 mole), carbon disulfide (15.2 grams, 0.20 mole), and dimethylammonium dimethyldithiocarbamate (33.2 grams, 0.20 mole) were dissolved in methanol (100 ml.). A mildly exothermic reaction resulted. After 21.5 hours, the reaction mixture was poured into water (850 ml.) and the precipitated oil was washed with water and then taken up in methylene chloride. The dried solution was concentrated in a rotary evaporator to leave an amber oil. A small sample of the product was chromatographed on Florisil adsorbant giving an oil which solidified when chilled in methanol solution. The main sample crystallized from cold methanol solution when it was seeded. Repeated recrystallization from cold methanol gave pure 2-nitrobutyl dimethyldithiocarbamate melting at about 23° C. The structure was determined from infrared and nuclear magnetic resonance spectra and elemental analysis.

1. customA mildly exothermic reaction
2. customresulted
3. washthe precipitated oil was washed with water
4. concentrationThe dried solution was concentrated in a rotary evaporator
5. customto leave an amber oil
6. customA small sample of the product was chromatographed on Florisil adsorbant
7. customgiving an oil which
8. customThe main sample crystallized from cold methanol solution when it
9. customrecrystallization from cold methanol

ORD record

ord-b709b60b79784e259038ae948df0ee40

Source dataset

uspto-grants-1977_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04038288