2,4-Dichloro-N-methoxy-N-methylbenzamide synthesis

7synthesis methods

Product Name:2,4-Dichloro-N-methoxy-N-methylbenzamide
CAS Number:646528-36-1
Molecular formula:C9H9Cl2NO2
Molecular Weight:234.08

6638-79-5 Synthesis

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2,4-Dichloro-N-methoxy-N-methylbenzamide

646528-36-1
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$130.78/1gm:

Yield:646528-36-1 100%

Reaction Conditions:

with pyridine in dichloromethane at 0; for 6 h;

Steps:

2.A

2,4-Dichlorobenzoyl chloride (11.59 g, 7.76 mL, 55.3 mmoles) and N,O-dimethylhyoxy]amine hydrochloride (4.91 g, 50.3 mmoles) were dissolved in anhydrous dichloromethane (550 mL) and the mixture was cooled to 0° C. under argon. Anhydrous pyridine (8.76 g, 8.96 mL, 110.6 mmoles) was added dropwise to the stirred solution at 0° C. and the mixture was stirred at 0° C. for 6 h. The mixture was evaporated to dryness and the residue was partitioned between diethyl ether-dichloromethane (1:1) and brine. The organic layer was dried (MgSO₄), filtered and evaporated to dryness. The residue was chromatographed on a silica gel column (60×5 cm) using 1% (10% conc. NH₄OH in methanol)-dichloromethane as the eluant to give the title compound as a colorless oil (11.78 g, 100%): ESMS: m/z234.0 (MH⁺); Found: C, 46.16; H, 3.55; Cl, 29.81; N, 5.96. C₉H₉Cl₂NO₂requires: C, 46.18; H, 3.88; Cl, 30.29; N, 5.98; δ_H(CDCl₃) 3.34 (3H, s, NCH₃), 3.48 (3H, s, OCH₃), 7.26 (2H, s, H₃, H₅) and 7.43 ppm (1H, s, H₆); δ_CCDCl₃) CH₃: 32.3, 61.5; CH: 127.0, 128.7, 129.6; CH: 127.0, 128.7 129.6: C: 131.8, 133.8, 135.6, 165.1.