1,3-Dibromopropane → N,N-dimethyl4 bromopropoxy-3-methoxybenzamide

HRID 2269945Notes

Reaction equation

HRID 2269945 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23][CH2:24]Br>C(#N)C>[CH3:14][N:2]([CH3:1])[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:24][CH2:23][CH2:22][Br:21])=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 21747248HCID 21747248, compound

Product 1

HCID 10358359N,N-dimethyl4 bromopropoxy-3-methoxybenzamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To N,N-dimethyl-4-hydroxy-3-methoxybenzamide (5.64 g, 28.7 mmol) in acetonitrile (450 ml) was added potassium carbonate (7.9 g) followed by 1,3-dibromopropane (11.6 g). The resulting reaction mixture was refluxed for 3 hours and stirred at room temperature for 12 hours. The mixture was filtered and concentrated to an oil. Following purification by column chromatography, N,N-dimethyl-4-bromopropoxy-3-methoxybenzamide as a colorless oil (7.6 g) was obtained.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 3 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to an oil
  5. custompurification by column chromatography

Sources & evidence

ORD record
ord-cf6c61b24aae460ea55fe26d6178c009
Source dataset
uspto-grants-2001_12
Patent number
USRE037478E1

Reaction notes

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