Tetrahydrofuran → 2-Bis(p-dimethylaminophenyl)Methoxy Acetanilide

HRID 66927

Reaktionsgleichung

Reaktionsgleichung von HRID 66927
[OH:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:12][N:13]([C:15]1[CH:31]=[CH:30][C:18]([CH:19](O)[C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1)[CH3:14].COC.O1CCCC1>CS(O)(=O)=O.CN(C)C(=N)N(C)C.CCCCCC>[CH3:28][N:26]([CH3:27])[C:23]1[CH:22]=[CH:21][C:20]([CH:19]([C:18]2[CH:30]=[CH:31][C:15]([N:13]([CH3:14])[CH3:12])=[CH:16][CH:17]=2)[O:1][CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])=[CH:25][CH:24]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 927424,4'-Bis(dimethylamino)benzhydrolHCID 2642602-Hydroxy-N-phenylacetamide

Produkt 1

HCID 204880412-Bis(p-dimethylaminophenyl)Methoxy Acetanilide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6395Methanesulfonic AcidKatalysatorHCID 664601,1,3,3-TetramethylguanidineKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of alpha-hydroxyacetanilide (3.62 g, 0.024 mole), 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (6.81 g, 0.024 mole) 50 ml of tetrahydrofuran, 153 ml of n-hexane, and one drop of methanesulfonic acid was refluxed for 11 hours, during which time an additional 300 ml of solvent was added. The blue-green solution was decolorized with 4 drops of tetramethylguanidine and the reaction mixture was filtered hot and the filtrate chilled. Yellow-green crystals formed, which were recrystallized from 30 ml petroleum ether/15 ml acetone to give a white solid, mp 118°-128° C.

Aufarbeitung

  1. additionwas added
  2. filtrationthe reaction mixture was filtered hot
  3. temperaturethe filtrate chilled
  4. customYellow-green crystals formed
  5. customwhich were recrystallized from 30 ml petroleum ether/15 ml acetone
  6. customto give a white solid, mp 118°-128° C.

Quellen und Nachweise

ORD-Eintrag
ord-a51f038435e34d9bbc72f79b2f35dec5
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343939

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