Ethylmethyl-carbamic chloride Chemical Properties

Boiling point:

89°C/40mmHg(lit.)

Density 

1.101±0.06 g/cm3(Predicted)

refractive index 

1.4500-1.4540

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

pka

-1.85±0.70(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

Stability:

Hygroscopic

InChI

InChI=1S/C4H8ClNO/c1-3-6(2)4(5)7/h3H2,1-2H3

InChIKey

XZVYDRLPXWFRIS-UHFFFAOYSA-N

SMILES

C(Cl)(=O)N(CC)C

CAS DataBase Reference

42252-34-6(CAS DataBase Reference)

Safety Information

RIDADR 

3265

HazardClass 

8

PackingGroup 

II

HS Code 

2924190015

Ethylmethyl-carbamic chloride Usage And Synthesis

Uses

N-Ethyl-N-methylcarbamoyl chloride is used as an intermediate for rivastigmine.

Uses

N-Ethyl-N-methylcarbamoyl chloride is a compound that can be used in organic synthesis.

Chemical Properties

Pale Yellow Oil

Synthesis

Example 1: A solution of N-ethylmethylamine (100 g, 1.69 mol) in dichloromethane (1.5 L) was slowly added dropwise to a suspension in dichloromethane (2 L) containing sodium bicarbonate (284 g, 3.384 mol) and triphosgene (332 g, 1.117 mol), the temperature was maintained at a controlled level of 10-15°C, and the dropwise process lasted for 2 hours. After completion of the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 3 hours. Upon completion of the reaction, the resulting sodium chloride was removed by filtration and the filtrate was concentrated under reduced pressure to afford 189 g of N-methyl-N-ethylcarbamoyl chloride, the product being a light yellow oil (yield: 92%). Example 3: The procedure of Example 2 was repeated, only the solvent was changed to methylene chloride, and the rest of the reaction conditions remained unchanged. The experimental results are shown in Table 2, the yield consistently exceeded 98%.

References

[1] Patent: WO2007/80430, 2007, A1. Location in patent: Page/Page column 12; 13
[2] Research on Chemical Intermediates, 2014, vol. 40, # 2, p. 787 - 800
[3] Patent: WO2013/150529, 2013, A2. Location in patent: Page/Page column 24; 25; 28; 29
[4] Patent: WO2007/80430, 2007, A1. Location in patent: Page/Page column 13
[5] Patent: WO2007/80430, 2007, A1. Location in patent: Page/Page column 13

Ethylmethyl-carbamic chloride(42252-34-6)Related Product Information

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• Ethyl acetate
• Ethyl cyanoacetate
• Ethyl formate
• Sodium chloride
• Zinc chloride
• Ethanesulfonyl chloride
• Oxalyl chloride
• p-Toluoyl chloride
• Ethyl acrylate
• Calcium chloride
• Ethyl pyruvate
• Ethanol
• Ethyl oleate
• Ammonium chloride
• Choline chloride
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• Potassium chloride