| Identification | More | [Name]
N-Methoxy-N-methylacetamide | [CAS]
78191-00-1 | [Synonyms]
N-ACETYL-N,O-DIMETHYLHYDROXYLAMINE
N-METHOXY-N-METHYLACETAMIDE
N-METHOXY-N-METHLACETAMIDE
N-Methoxy-N-methylacetamide, 98 %
N-Methyl-N-methoxyacetamide | [EINECS(EC#)]
628-920-3 | [Molecular Formula]
C4H9NO2 | [MDL Number]
MFCD00060098 | [Molecular Weight]
103.12 | [MOL File]
78191-00-1.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Boiling point ]
152 °C (lit.) | [density ]
0.97 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.426(lit.)
| [Fp ]
121 °F
| [storage temp. ]
Flammables area | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Colorless | [Water Solubility ]
Soluble | [InChI]
InChI=1S/C4H9NO2/c1-4(6)5(2)7-3/h1-3H3 | [InChIKey]
OYVXVLSZQHSNDK-UHFFFAOYSA-N | [SMILES]
C(N(OC)C)(=O)C | [CAS DataBase Reference]
78191-00-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless liquid | [Uses]
N-Methoxy-N-methylacetamide, is a Weinreb amide used in the synthesis of marine natural products myriaporone and usneoidone as a ketone synthon. | [Preparation]
N-Methoxy-N-methylacetamide can be prepared by reaction of Acetyl Chloride with commercially available N,O-Dimethylhydroxylamine hydrochloride in pyridine, followed by distillation at reduced pressure (65%). | [General Description]
Simple Weinreb amide used in the synthesis of marine natural products myriaporone and usneoidone as a ketone synthon. | [Synthesis]
N-Methoxy-N-methylacetamide (105) was synthesized as follows: pyridine (10 mL, 124 mmol) was slowly added dropwise to a well-stirred suspension of O,N-dimethylhydroxylamine hydrochloride (6 g, 62 mmol) and acetyl chloride (4.15 mL, 59 mmol) in dichloromethane (85 mL) under argon protection. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. Subsequently, the reaction mixture was partitioned between brine (55 mL) and ether (85 mL). The aqueous phase was extracted with additional ether and the combined organic layers were dried over anhydrous sodium sulfate, concentrated and purified by reduced pressure distillation to afford Weinreb amide 105 (4.54 g, 72% yield) as a colorless liquid. The boiling point of the product was 42-44 °C/20 mmHg; IR (pure sample) showed absorption peaks located at 3497, 2971, 2941, 2824, 1663 cm-1; 1H NMR (CDCl3, 300 MHz) δ 3.62 (s, 3H), 3.11 (s, 3H), 2.05 (s, 3H); 13C NMR (CDCl3. 75.4 MHz) δ 171.8 (C), 61.0 (CH3), 31.9 (CH3), 19.6 (CH3). The spectral data of the obtained products are in agreement with literature reports. | [storage]
N-Methoxy-N-methylacetamide is stable but should be protected from moisture; use in a fume hood. | [References]
[1] Organic Letters, 2012, vol. 14, # 9, p. 2250 - 2253
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 2, p. 278 - 286
[3] Patent: EP1300403, 2003, A1
[4] Tetrahedron Letters, 1983, vol. 24, # 18, p. 1851 - 1854
[5] Tetrahedron Letters, 2007, vol. 48, # 3, p. 377 - 380 |
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