ChemicalBook CAS DataBase List 3-CHLORO-N-METHOXY-N-METHYLBENZAMIDE

3-CHLORO-N-METHOXY-N-METHYLBENZAMIDE synthesis

9synthesis methods

Product Name:3-CHLORO-N-METHOXY-N-METHYLBENZAMIDE
CAS Number:145959-21-3
Molecular formula:C9H10ClNO2
Molecular Weight:199.63

873-63-2 Synthesis

873-63-2
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$6.00/5g

6638-79-5 Synthesis

6638-79-5
587 suppliers
$6.00/25g

145959-21-3
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$52.50/250mg

Yield:145959-21-3 90%

Reaction Conditions:

with tert.-butylhydroperoxide;copper(II) acetate monohydrate;calcium carbonate in acetonitrile at 80; for 24 h;

Steps:

Oxidative Synthesis of Weinreb Amides 3 from Benzyl Alcohols 1 and N,O-Dimethylhydroxylamine Hydrochloride Salt (2); General Procedure

General procedure: An oven-dried 15 mL glass vial with a magnetic stirrer bar was charged with Cu(OAc)₂·H₂O (12 mg, 6 mol%), N,O-dimethylhydroxylamine hydrochloride (2; 117 mg, 1.2 mmol), the respective benzyl alcohol 1 (1 mmol), aq 70% TBHP (0.17 mL, 1.2 mmol), CaCO₃ (120 mg, 1.2 mmol) in MeCN (1 mL). The glass vial was flushed with N₂ three times and the contents were stirred at r.t. for 1 h. Then the reaction mixture was stirred for 24 h at 80 °C. After completion of the reaction, the mixture was cooled to r.t. All volatiles were removed under vacuum. The product was extracted with EtOAc (20 mL) and the organic layer was washed with sat. aq NaHCO₃ (20 mL), dried (Na₂SO₄), and the solvent removed under vacuum. The Weinreb amide product 3 was purified by column chromatography (silica gel, 100-200 mesh) using a gradient of petroleum ether (bp 60-80 °C) and EtOAc. All the amides were identified by GC-MS, ¹H, and ¹³C NMR spectroscopic analysis.

References:

Yedage, Subhash L.;Bhanage, Bhalchandra M. [Synthesis,2015,vol. 47,# 4,art. no. SS-2014-T0513-OP,p. 526 - 532]

6638-79-5 Synthesis

6638-79-5
587 suppliers
$6.00/25g