3,4-Dichlorobenzoic acid → 3,4-Dichloro-N-methoxy-N-methylbenzamide

HRID 23527Notes

Reaction equation

HRID 23527 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O>[CH3:16][O:15][N:14]([CH3:13])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=1

Participants

7

Reactant 4

HCID 58173,4-Dichlorobenzoic acidHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 114136423,4-Dichloro-N-methoxy-N-methylbenzamideYield 94.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3,4-dichlorobenzoic acid (1.0 g, 5.24 mmol) in CH2Cl2 (25 mL) was added N,O-dimethylhydroxylamine hydrochloride (613 mg, 6.28 mmol) followed by N-methylmorpholine (865 μL, 7.85 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 g, 6.28 mmol) at which point the reaction mixture became homogeneous. After 2 h, the reaction mixture was diluted with EtOAc and washed with 1N HCl, H2O, saturated NaHCO3 solution and brine, sequentially. The organic layer was dried over Na2SO4, and the removal of solvent in vacuo gave the title compound (1.16 g) that required no further purification.

Workup

  1. washwashed with 1N HCl, H2O, saturated NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe removal of solvent in vacuo

Sources & evidence

ORD record
ord-387d71719b3a46319e14a0312e9bedf3
Source dataset
uspto-grants-2005_02
Patent number
US06852727B2

Reaction notes

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