2-CHLORO-N-METHOXY-N-METHYLACETAMIDE Chemical Properties

Melting point:

39-41 °C(lit.)

Boiling point:

94-95 °C

Density 

1.178±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

220 °F

storage temp. 

2-8°C

form 

Crystals

color 

White to light yellow

Water Solubility 

Insoluble in water.

BRN 

1924015

InChI

InChI=1S/C4H8ClNO2/c1-6(8-2)4(7)3-5/h3H2,1-2H3

InChIKey

SCOJKGRNQDKFRP-UHFFFAOYSA-N

SMILES

C(N(OC)C)(=O)CCl

CAS DataBase Reference

67442-07-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

23-26-27-28-37/39

WGK Germany 

3

HS Code 

29241900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-CHLORO-N-METHOXY-N-METHYLACETAMIDE Usage And Synthesis

Chemical Properties

white to light yellow crystals

Uses

2-Chloro-N-methoxy-N-methylacetamide is used in the preparation of 2-heptyl-3-hydroxy-4(1H)-quinolone (Pseudomonas quinolone signal or PQS) and structurally related 2-alkyl-4-quinolones having biological activity, 2-(benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide and α-chloro-ketone, starting reagent for the one-pot synthesis of 2-heptyl-3-hydroxyl-4(1H)-quinolone (PQS), signaling molecule in the quorum sensing of Pseudomonas aeruginosa.

General Description

2-Chloro-N-methoxy-N-methylacetamide is a Weinreb amide.

Synthesis

Example 139 Synthesis of N-methoxy-N-methylchloroacetamide: N,O-dimethylhydroxylamine hydrochloride (200 g, 2.05 mol) was dissolved in tert-butyl methyl ether (2 L), and the solution was slowly added to an aqueous solution of potassium carbonate (624 g, 4.1 mol) (2 L) that was pre-cooled to 0 °C. The reaction mixture was further cooled to -5 °C, followed by the slow dropwise addition of chloroacetyl chloride, controlling the reaction temperature to not exceed 5 °C. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature with continuous vigorous stirring for 3.5 hours. After completion of the reaction, the organic and aqueous phases were separated and the aqueous phase was extracted with tert-butyl methyl ether (3 x 1 L). All organic phases were combined, washed with saturated aqueous sodium chloride solution (2 x 1 L), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dried under vacuum to give a white solid product (257 g, 92% yield). The product was characterized by the following data: melting point 39-40.5 °C; 1H NMR (CDCl3, 300 MHz) δ 4.24 (s, 2H), 3.74 (s, 3H), 3.22 (s, 3H); mass spectra (CI) m/z 138 (MH+); elemental analysis (C4H8ClNO2) calculated values: C, 34.92; H, 5.86; N, 10.18; measured values. 10.18; measured values: C, 35.06; H, 5.88; N, 10.23.

References

[1] Journal of the American Chemical Society,
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 1077 - 1091
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 27, p. 3917 - 3920
[4] RSC Advances, 2013, vol. 3, # 26, p. 10158 - 10162
[5] Patent: EP1054881, 2008, B1. Location in patent: Page/Page column 57

2-CHLORO-N-METHOXY-N-METHYLACETAMIDE(67442-07-3)Related Product Information

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