o-Benzylbenzoic acid → 2-benzyl-N-methylbenzamide

HRID 2196380Notes

Reaction equation

HRID 2196380 reaction equation
[C:1]1([CH2:7][C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.Cl.CN.[CH:26]([N:29](CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O>[CH3:26][NH:29][C:14](=[O:16])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 11924o-Benzylbenzoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochloride

Product 1

HCID 41285092-benzyl-N-methylbenzamideYield 44,856.801%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent4×

Procedure

To a stirred solution of α-phenyl-o-toluic acid (2.0 g, 9.43 mmol) in methylene chloride (500 mL) at room temperature under argon was added by dropwise addition a solution of oxalyl chloride (0.988 mL, 11.3 mmol) in methylene chloride (50 mL). N,N-Dimethylformamide (10 drops) were added and the contents of the reaction flask were stirred 1.5 h. Solvent was removed in vacuo and methylene chloride (100 mL) and methylamine hydrochloride (950 mg, 14.1 mmol) was added. With ice-bath cooling a solution of N,N-diisopropylethylamine (4.10 mL, 23.6 mmol) in methylene chloride (10 mL) was added dropwise. Saturated sodium bicarbonate was added and the resulting mixture extracted with methylene chloride (3×). The combined organic extracts were dried with sodium sulfate (anh.). Filtration followed by removal of the solvent in vacuo gave a solid which after trituration with ether afforded N-Methyl-2-(phenylmethyl)benzamide (974 mg, 4.23 mol, 46%). MS [M+H]+ 226

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. extractionthe resulting mixture extracted with methylene chloride (3×)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate (anh.)
  5. filtrationFiltration
  6. customfollowed by removal of the solvent in vacuo
  7. customgave a solid which after trituration with ether

Sources & evidence

ORD record
ord-4e051715dadc4ef7b90058ce0d540bb4
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

Loading…