Benzoic Acid → N-Methoxy-N-methylbenzamide

HRID 402470Notes

Reaction equation

HRID 402470 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[C:6]([OH:14])(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>ClCCl>[CH3:5][O:4][N:3]([CH3:2])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 569575N-Methoxy-N-methylbenzamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,O-dimethyl hydroxyl amine hydrochloride (4.393 g, 45.037 mmol) was added to a stirred solution of benzoic acid (5.0 g, 40.943), EDC.HCl (9.418 g, 49.132) and N-methyl morpholine (4.141 g, 40.943 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at rt for 4 h. After completion of the reaction, the reaction mixture was concentrated. Diethyl ether was added and the mixture was extracted with water and brine. The organic layer was dried over Na2SO4 and filtrated. Concentration of the organic layer furnished the title compound as a colorless liquid (4.933 g, 73%). [1H-NMR (CDCl3, 300 MHz) δ 7.72-7.64 (m, 2H), 7.52-7.36 (m, 3H), 3.58 (s, 3H), 3.38 (s, 3H); HPLC RtA=6.281 min. (98%); LCMS RtA=0.38 min; [M+H]+=166.1]

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. additionDiethyl ether was added
  4. extractionthe mixture was extracted with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltrated

Sources & evidence

ORD record
ord-96ef433e3ae84a56a80b4c26208537ee
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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