Boron trifluoride etherate → N-(2-chlorobenzyl)-3-methoxyphenylacetamide

HRID 359979

Reaktionsgleichung

Reaktionsgleichung von HRID 359979
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(N(CC)CC)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 15719(3-Methoxyphenyl)acetic acidHCID 666482-Chlorobenzylamine

Produkt 1

HCID 2089226N-(2-chlorobenzyl)-3-methoxyphenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 12.5 g of 3-methoxyphenylacetic acid, 21.2 g of 2-chlorobenzylamine, 15.1 g of triethylamine, 19.3 ml of borontrifluoride etherate, and 500 ml of toluene was stirred under reflux for 18 hours using a Dean-Stark moisture trap and allowed, to cool. The mixture was extracted with aqueous sodium hydroxide, dilute hydrochloric acid, and water. The remaining organic solution was then evaporated and the residue crystallized from hexane to yield N-(2-chlorobenzyl)-3-methoxyphenylacetamide as a yellow solid, m.p. 89°-91° C.

Aufarbeitung

  1. temperatureunder reflux for 18 hours
  2. temperatureto cool
  3. extractionThe mixture was extracted with aqueous sodium hydroxide, dilute hydrochloric acid, and water
  4. customThe remaining organic solution was then evaporated
  5. customthe residue crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-cded4afd5f1e40a7a1aa6af296d4de54
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05003106

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