Oxalyl chloride → 2-Benzyl-4-methoxy-N-methylbenzamide

HRID 985149Notes

Reaction equation

HRID 985149 reaction equation
[CH2:1]([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.CN.[CH:28]([N:31](C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C.CCCCCC.CCOCC>[CH2:1]([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([NH:31][CH3:28])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 225559782-Benzyl-4-methoxybenzoic acid

Product 1

HCID 225559272-Benzyl-4-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 21584099Diethylether hexaneSolvent

Procedure

To an ice bath cooled solution of 10 (11.8 g, 48.8 mmol) in methylene chloride under Argon was added oxalyl chloride (5.10 mL, 58.5 mmol). Added a few drops of DMF and warmed to room temperature. After 18 h the solvent was removed in vacuo. Methylene chloride and methylamine hydrochloride (6.54 g, 97.6 mmol) were added and the contents of the reaction flask were cooled in an ice bath. Diisopropylethylamine was added dropwise using an addition funnel. After 3 h the reaction solution was washed with 5% potassium bisulfate, sat. sodium bicarbonate, and brine. Dried the organic layer with sodium sulfate (anh.) and removed the solvent in vacuo. Trituration with hexane/ether gave 11 as a light solid (8.15 g, 32.0 mmol, 65.5%).

Workup

  1. customAfter 18 h the solvent was removed in vacuo
  2. temperaturethe contents of the reaction flask were cooled in an ice bath
  3. washAfter 3 h the reaction solution was washed with 5% potassium bisulfate, sat. sodium bicarbonate, and brine
  4. dry with materialDried the organic layer with sodium sulfate (anh.)
  5. customremoved the solvent in vacuo

Sources & evidence

ORD record
ord-533d2d7139c94c1e8d30940383fe214b
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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