Dimethylformamide → 3-(4-bromophenyl)-N-methylpropanamide

HRID 746761Notes

Reaction equation

HRID 746761 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1.[CH3:19][N:20](C=O)C.CN>C(Cl)Cl.C1COCC1.O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([NH:20][CH3:19])=[O:18])=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 178950553-(4-bromophenyl)-N-methylpropanamideYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add oxalyl chloride (1.75 mL, 2.54 g, 4 eq.) to a solution of 3-(4-bromo-phenyl)-propionic acid in methylene chloride (100 mL), which contains 0.1 mL DMF at 0° C. and allow the reaction mixture to warm to room temperature and stir 1 hour. Evaporate solvent and dissolve it in 10 mL THF. Add half of the THF solution to 20 mL of methylamine (2M) and stir another hour. Add water to the solution to dissolve solid and wash organic layer with 2N HCl, water and saturated aq. sodium chloride and dry it over MgSO4. Evaporate solvent to afford the title compound 500 mg, 41%. MS 246.0.

Workup

  1. customat 0° C.
  2. stirringstir another hour
  3. washwash organic layer with 2N HCl, water and saturated aq. sodium chloride
  4. dry with materialdry it over MgSO4

Sources & evidence

ORD record
ord-4e22665ef614418b869b1e3e5ea97d0d
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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