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Ethylmethyl-carbamic chloride

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Ethylmethyl-carbamic chloride Basic information
Uses Application
Product Name:Ethylmethyl-carbamic chloride
Synonyms:N,N-ETHYLMETHYL CARBAMOYL CHLORIDE;N-ETHYL-N-METHYLCARBAMONYL CHLORIDE;CarbaMic chloride,N-ethyl-N-Methyl-;Rivastigmine Intermediate 1;Ethylmethyl-carbamic chloride;CARBAMIC CHLORIDE, ETHYLMETHYL-;ETHYLMETHYLCARBAMOYL CHLORIDE;cis-2-(2-benzylcarboxylamido-4-thiazolyl)-4-(3-methyl-2-butyleneoxycarboxyl)-2-butenoicacid
CAS:42252-34-6
MF:C4H8ClNO
MW:121.57
EINECS:610-003-4
Product Categories:Miscellaneous Reagents
Mol File:42252-34-6.mol
Ethylmethyl-carbamic chloride Structure
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)
form clear liquid
pka-1.85±0.70(Predicted)
color Colorless to Almost colorless
Stability:Hygroscopic
InChIInChI=1S/C4H8ClNO/c1-3-6(2)4(5)7/h3H2,1-2H3
InChIKeyXZVYDRLPXWFRIS-UHFFFAOYSA-N
SMILESC(Cl)(=O)N(CC)C
CAS DataBase Reference42252-34-6(CAS DataBase Reference)
Safety Information
RIDADR 3265
HazardClass 8
PackingGroup II
HS Code 2924190015
MSDS Information
Ethylmethyl-carbamic chloride Usage And Synthesis
UsesN-Ethyl-N-methylcarbamoyl chloride is used as an intermediate for rivastigmine.
ApplicationN-Ethyl-N-methylcarbamoyl chloride is a compound that can be used in organic synthesis.
Chemical PropertiesPale Yellow Oil
Synthesis
N-Ethylmethylamine

624-78-2

Triphosgene

32315-10-9

Ethylmethyl-carbamic chloride

42252-34-6

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
Ethylmethyl-carbamic chloride Preparation Products And Raw materials
Raw materialsN-Ethylmethylamine-->Triphosgene-->Sodium bicarbonate-->Dichloromethane
Preparation ProductsRivastigmine-->Rivastigmine hydrochloride
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