Triethylamine → 2-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 2212182

Reaction equation

HRID 2212182 reaction equation
C(N(CC)CC)C.[Br:8][CH2:9][C:10](Br)=[O:11].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[NH2:18]>O1CCCC1>[Br:8][CH2:9][C:10]([NH:18][C:17]1[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 322853,4,5-TrimethoxyanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 219637112-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add triethylamine (1.53 mL, 11.0 mmol) and bromoacetyl bromide (0.87 mL, 10.0 mmol) dropwise to a 0° C. solution of 3,4,5-trimethoxy-aniline (1.74 g, 9.5 mmol) in tetrahydrofuran (30 mL). Allow the reaction to warm to room temperature overnight. Filter the mixture, wash with tetrahydrofuran, and concentrate. Dissolve the resulting brown solid in chloroform; wash with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform) to give 2.50 g of the title compound as an orange solid, 87% yield. 1H NMR: consistent with structure. MS (ion spray) 304 (M+).

Workup

  1. customthe reaction
  2. filtrationFilter the mixture
  3. washwash with tetrahydrofuran
  4. concentrationconcentrate
  5. dissolutionDissolve the resulting brown solid in chloroform
  6. washwash with 1N HCl, saturated aqueous sodium bicarbonate solution, and brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationand concentrate
  9. customPurify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform)

Sources & evidence

ORD record
ord-038dd8b7cf0c49c0919656a02eb5a167
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Linked notes

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