p-Toluenesulfonic acid → HCID 178491344, Verbindung

HRID 254461

Reaktionsgleichung

Reaktionsgleichung von HRID 254461
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=O.[NH2:13][CH:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1/[CH:5]=[N:13]/[CH:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 777023-Pentanamine, 2,4-dimethyl-HCID 964042,6-Dimethoxybenzaldehyde

Produkt 1

HCID 178491344HCID 178491344, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 25.0 g (150 mmol) 2,6-dimethoxybenzaldehyde, 19.1 g (165 mmol) 3-amino-2,4-dimethylpentane and 0.500 g p-toluenesulfonic acid in 100 ml toluene was heated in a Dean-Stark apparatus to reflux for 2 hours. Then the cooled reaction mixture was washed with aqueous NaHCO3 solution, brine dried over Na2SO4, filtered and evaporated. The crude product was filtered through a silica pad with heptane/ethyl acetate 2:1 as eluent: 22.0 g [1-(2,6-dimethoxy-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine as slightly yellow crystals: MS (EI): 264.3 ((M+H)+.), 262.3 ((M-H)+.), 248.3 ((M−CH3)+.), 220.2 ((M−(CH3)2CH)+.), 100%).

Aufarbeitung

  1. temperaturewas heated in a Dean-Stark apparatus
  2. temperatureto reflux for 2 hours
  3. customThen the cooled reaction mixture
  4. washwas washed with aqueous NaHCO3 solution, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe crude product was filtered through a silica pad with heptane/ethyl acetate 2:1 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d89bcb139b314bc49a6166f783772c3f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875645B2

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