N-Cyanoimido-S,S-dimethyl-dithiocarbonate synthesis
- Product Name:N-Cyanoimido-S,S-dimethyl-dithiocarbonate
- CAS Number:10191-60-3
- Molecular formula:C4H6N2S2
- Molecular Weight:146.23
75-15-0
420-04-2
74-88-4
10191-60-3
Dimethyl N-cyanoimido-S,S-dithiocarbonate was synthesized according to the method reported in the literature. The procedure was as follows: cyanamide (0.02 mol, 50% aqueous solution) was dissolved in 80 mL of water, followed by addition of potassium hydroxide (0.04 mol) and stirred for 45 min at room temperature. Carbon disulfide was then added and the reaction mixture was heated to 40°C. After complete dissolution of carbon disulfide (about 2 hours), iodomethane (0.04 mole) was added and stirred overnight at room temperature. After completion of the reaction, the precipitate was collected by filtration, the solid product was washed with water, dried under vacuum at room temperature to constant weight and finally purified by recrystallization from ethanol. The resulting product was dimethyl cyanodithioiminocarbonate (1c) in 71% yield with a melting point of 58-60°C. Infrared spectra (FT-IR, ν/cm?1): 1678, 2176. nuclear magnetic resonance hydrogen spectra (1H NMR, 300 MHz, DMSO-d6) δ: 2.90 (s, 6H, 2×SCH3). NMR carbon spectra (13C NMR, 75 MHz, CDCl3) δ: 18.8, 115.3, 186.8.
75-15-0
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420-04-2
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77-78-1
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10191-60-3
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Yield:10191-60-3 93%
Reaction Conditions:
Stage #1:CYANAMID with potassium hydroxide in acetone for 0.25 h;
Stage #2:carbon disulfide in acetone at 10 - 15; for 2 h;
Stage #3:dimethyl sulfate at 40 - 45; for 6 h;
Steps:
1 Example 1
Add 40percent potassium hydroxide solution (70 g, 0.5 mol) to a mixed solution of 75 ml acetone and 30percent amine cyanide (35 g, 0.25 mol) while stirring.The addition is completed in 15 minutes.The temperature of the reaction system was reduced to 10-15°C, carbon disulfide (19.5 g, 0.254 mol) was added, and the temperature was maintained at 10-15°C for 2 hours.Raise the temperature to 2025, stand for layering, recover the organic layer, and heat the water layer to 4045,Dimethyl sulfate (64 g, 0.5 mol) was added dropwise to the water layer, and the addition was completed in 1 hour.The reaction mixture is heated to reflux for 5 hours, then the temperature is lowered to 5-10°C, and the temperature is maintained for 0.5 hours.The precipitate separated out, filtered, and dried to obtain 33.9 g of light yellow intermediate II with a yield of 93percent.
References:
Qingdao Agricultural University;Li Yuwen;Ma Cuili CN111440127, 2020, A Location in patent:Paragraph 0007
75-15-0
266 suppliers
$40.00/100 g
420-04-2
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$15.00/25g
74-88-4
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$15.00/10g
10191-60-3
213 suppliers
$6.00/5g
75-15-0
266 suppliers
$40.00/100 g
156-62-7
112 suppliers
$29.12/25G
77-78-1
322 suppliers
$19.69/1ml
10191-60-3
213 suppliers
$6.00/5g
