Toluene → 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide

HRID 1767

Reaction equation

HRID 1767 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[O:6][CH3:7].C(N(CC)CC)C.C1(C)C=CC=CC=1.[Br:25][CH:26]([CH3:30])[C:27](Br)=[O:28]>O>[Br:25][CH:26]([CH3:30])[C:27]([N:2]([C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:1])=[O:28]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 84349N-Methyl-m-anisidine

Product 1

HCID 196929362-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-methyl-m-anisidine (265 g), triethylamine (269 ml) and toluene (550 ml) was stirred at 0° C. as 2-bromopropionyl bromide (202.6 ml) was added dropwise. The mixture was mechanically stirred overnight at room temperature. Water was added to the reaction and the aqueous layer was collected and extracted with ethyl acetate. All organic phases were combined, washed with 2N HCl, and dried (Na2SO4). The solvent was evaporated to yield an oil which was purified using Kugelrohr distillation. The distillate was dissolved in isopropyl ether. The solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution.

Workup

  1. additionwas added dropwise
  2. customthe aqueous layer was collected
  3. extractionextracted with ethyl acetate
  4. washwashed with 2N HCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customto yield an oil which
  8. customwas purified
  9. distillationKugelrohr distillation
  10. dissolutionThe distillate was dissolved in isopropyl ether
  11. customThe solid product, 2-Bromo-N-(3-methoxyphenyl)-N-methyl-propanamide, m.p. 55°-56° C., crystallized from this solution

Sources & evidence

ORD record
ord-8b32fa3382184901ae70790edf4034ba
Source dataset
uspto-grants-1998_03
Patent number
US05726323

Linked notes

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