| Identification | More | [Name]
2-CHLORO-N-METHOXY-N-METHYLACETAMIDE | [CAS]
67442-07-3 | [Synonyms]
2-CHLORO-N-METHOXY-N-METHYLACETAMIDE
2-CHLORO-N-METHOXY-N-METHYLACETAMIDE, 98 %
Methyl 2-Chloro-N-methylacetohydroxamate | [Molecular Formula]
C4H8ClNO2 | [MDL Number]
MFCD00134232 | [Molecular Weight]
137.56 | [MOL File]
67442-07-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystals | [Melting point ]
39-41 °C(lit.) | [Boiling point ]
94-95 °C | [density ]
1.178±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
220 °F
| [storage temp. ]
Refrigerator | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29241900 |
| Hazard Information | Back Directory | [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 |
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