Dimethylformamide → 4-Methoxybenzamide

HRID 2240203Notes

Reaction equation

HRID 2240203 reaction equation
C([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])C1C=CC=CC=1.C[N:20](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:9]([C:10]([NH2:20])=[O:11])=[CH:8][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 225559782-Benzyl-4-methoxybenzoic acid

Product 1

HCID 769594-Methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-benzyl-4-methoxybenzoic acid (14.2 g) in 600 mL CH2Cl2 was added a catalytic amount of DMF, followed by a solution of oxalyl chloride (8.7 g) in 100 mL of CH2Cl2. The reaction was stirred at room temp overnight, then concentrated and azeotroped with toluene (2×). The residue was dissolved in 700 mL CH2Cl2 and cooled to 0 C. Tert-butyl amine (13.9 g) was added, and the reaction was warmed to room temp. After 1.5 h, the reaction was quenched with 5% aqueous KHSO4. The organic solution was separated, washed once with saturated aqueous sodium bicarbonate, dried (Na2SO4) and concentrated to give 15.9 g of 2-benzyl-N-tert-butyl)-4-methoxybenzamide.

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene (2×)
  3. dissolutionThe residue was dissolved in 700 mL CH2Cl2
  4. temperaturecooled to 0 C
  5. additionTert-butyl amine (13.9 g) was added
  6. temperaturethe reaction was warmed to room temp
  7. waitAfter 1.5 h
  8. customthe reaction was quenched with 5% aqueous KHSO4
  9. customThe organic solution was separated
  10. washwashed once with saturated aqueous sodium bicarbonate
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7b726dcc643e41839b95d12f44fe52b9
Source dataset
uspto-grants-2010_05
Patent number
US07723352B2

Reaction notes

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