Ammonium Hydroxide → 4-BroMo-benzenepropanaMide

HRID 2220403Notes

Reaction equation

HRID 2220403 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[OH-].[NH4+:14]>S(Cl)(Cl)=O.CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:14])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 122731394-BroMo-benzenepropanaMide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 3-(4-bromophenyl)propanoic acid (15.0 g) in thionyl chloride (24.5 g) was added catalytic amount of N,N-dimethylformamide (one drop) and refluxed for 1.5 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured slowly into 28% aqueous ammonium hydroxide solution (150 ml) at 0° C. The mixture was extracted with ethyl acetate, washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 3-(4-bromophenyl)propanamide (13.7 g) as a white solid.

Workup

  1. temperaturerefluxed for 1.5 hours under nitrogen atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-12f1080491fe4e489b0dd82f8ea8d25e
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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