Ethoxycarbonyl Isothiocyanate

Chemical Properties

Light Yellow Oil

Uses

Versatile reagent for organic synthesis.
Ethoxycarbonyl isothiocyanate is used as a building block in the synthesis of various heterocycles. It is also used for the synthesis of 1,2,4-oxadiazolidine-3,5-dione. It is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

Ethoxycarbonyl isothiocyanate has been used in the synthesis of:

• pyrazolo[1,5-a][1,3,5]triazine derivatives, potential inhibitors of protein kinase CK2
• fused thiophene derivatives, having antibacterial and antifungal activities
• 4-thiouracil derivatives
• thiocarbamides from stannylarenes
• 1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines
• N-acylthioureas from aminodeoxy sugars

Application

Ethoxycarbonyl isothiocyanate reacts with 2-amino-tetrahydrobenzo[b]thiophene derivatives to yield tetrahydrobenzo[b]thiophen-2-thiourea derivatives.
Ethoxycarbonyl isothiocyanate has been used in the synthesis of:
pyrazolo[1,5-a][1,3,5]triazine derivatives, potential inhibitors of protein kinase CK2
fused thiophene derivatives, having antibacterial and antifungal activities
4-thiouracil derivatives
thiocarbamides from stannylarenes
1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines
N-acylthioureas from aminodeoxy sugars

Synthesis Reference(s)

Using Schiff base as a phase transfer catalyst, ethoxycarbonyl isothiocyanate was synthesized by reacting ethyl chloroformate with sodium thiocyanate. www.semanticscholar.org

General Description

Ethoxycarbonyl isothiocyanate reacts with 2-amino-tetrahydrobenzo[b]thiophene derivatives to yield tetrahydrobenzo[b]thiophen-2-thiourea derivatives.

Hazard

Lachrymator.

Synthesis

540-72-7

541-41-3

16182-04-0

Example 1: Preparation of ethoxycarbonyl isothiocyanate To a 1 liter jacketed reactor was added sodium thiocyanate (39.1 g, 0.48 mol) and 310 g of toluene. After heating the mixture to 30°C, pyridine (0.4 g, 0.005 mol) and water (0.9 g, 0.05 mol) were added sequentially. Subsequently, ethyl chloroformate (52.9 g, 0.49 mol) was added slowly and dropwise to the reaction system over 40 minutes. The reaction solution was maintained under stirring for 3 hours, during which time the progress of the reaction was monitored by gas chromatography (GC) to confirm that the ethyl chloroformate was almost completely consumed. Upon completion of the reaction, the reaction solution was filtered and analyzed by gas chromatography combined with quantitative internal standard method and the yield of ethoxycarbonyl isothiocyanate was measured to be 99%.

References

[1] Patent: US2014/100381, 2014, A1. Location in patent: Page/Page column
[2] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5230 - 5231
[3] Research on Chemical Intermediates, 2012, vol. 38, # 3-5, p. 903 - 909