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

HRID 233119
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 233119
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-34b65aea39294284a2c2c120ad95d1d0
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05591864

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