1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide

HRID 394888Notes

Reaction equation

HRID 394888 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[F:11].CCN=C=NCCCN(C)C.Cl.[CH3:24][NH:25][O:26][CH3:27]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:25]([O:26][CH3:27])[CH3:24])=[O:7])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 223138234-Bromo-3-fluoro-N-methoxy-N-methylbenzamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-3-fluorobenzoic acid (5.0 g, 22.83 mmol) in dichloromethane (100 ml) was added WSC (8.8 g, 45.66 mmol), N,O-dimethylhydroxylamine hydrochloride (4.5 g, 45.66 mmol) and stirred at room temperature for 5 h. The solvent was removed and the residue was diluted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), and concentrated to afford 5.47 g of the titled compound as a yellow oil. The compound was used for the next reaction directly.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b516732d87c74df9a5bec25b05d5f81f
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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