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

HRID 2212184

Reaktionsgleichung

Reaktionsgleichung von HRID 2212184
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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, brine; dry over magnesium sulfate; and concentrated. 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+).

Aufarbeitung

  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, brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationand concentrated
  9. customPurify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-7b4c6a6dcbcf45c9822c1cbb49c447dd
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101891B2

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