Pyridine → 3,5-Dichloro-N-methoxy-N-methylbenzamide

HRID 1865410Notes

Reaction equation

HRID 1865410 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](Cl)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 761913,5-Dichlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 587973333,5-Dichloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichlorobenzoyl chloride (5 g, 23.9 mmol) in 50 mL of dichloromethane at 0° C. was added N,O-dimethylhydroxylamine hydrochloride (2.56 g, 26.3 mmol) and pyridine (4.3 mL, 52.6 mmol). The cold bath was removed and the mixture stirred at ambient temperature for 16 hours, diluted with water and extracted with two portions of dichloromethane. The combined organic layers were dried over magnesium sulfate, concentrated in vacuo, and the residue purified by flash column chromatography (SiO2, 20% ethyl acetate/hexanes) to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ: 7.61 (d, J=1.9 Hz, 2H); 7.50 (d, J=1.9 Hz, 1H); 3.60 (s, 3H); 3.40 (s, 3H).

Workup

  1. customThe cold bath was removed
  2. additiondiluted with water
  3. extractionextracted with two portions of dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by flash column chromatography (SiO2, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7712bb65ec214df0a4f73b600a7889fa
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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