Methanimidamide, N,N-diphenyl- → 2-(2-Anilinovinyl)-3-ethyl-5-hexylsulfonamidobenzoxazolium p-toluenesulfonate

HRID 1199335

Reaktionsgleichung

Reaktionsgleichung von HRID 1199335
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([N+:14]1[C:18]2[CH:19]=[C:20]([NH:23][S:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:26])=[O:25])[CH:21]=[CH:22][C:17]=2[O:16][C:15]=1[CH3:33])[CH3:13].[C:34]1([N:40](C2C=CC=CC=2)[CH:41]=N)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH:40]([CH:41]=[CH:33][C:15]1[O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:25])=[O:26])=[CH:19][C:18]=2[N+:14]=1[CH2:12][CH3:13])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

4

Edukt 2

HCID 78296Methanimidamide, N,N-diphenyl-HCID 199934523-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

Produkt 1

HCID 867437442-(2-Anilinovinyl)-3-ethyl-5-hexylsulfonamidobenzoxazolium p-toluenesulfonateAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A combination of 10 g Intermediate B and 8 g N,N-diphenylformamidine was thoroughly mixed and heated with stirring at 150°-160° C. for 25 minutes. The flask was then fitted with a condenser and 50 ml hot acetone was cautiously added. An orange precipitate formed. The flask was removed from the heat, cooled, and chilled in ice. After 1 hour, the reddish precipitate was filtered off and discarded. The filtrate was poured into 300 ml diethyl ether and stirred for 2 hors. The resulting yellow-orange powder was filtered, washed with ether, and dried to yield 10.6 g of 2-(2-anilinovinyl)-3-ethyl-5-hexylsulfonamidobenzoxazolium p-toluenesulfonate (Intermediate C).

Aufarbeitung

  1. temperatureheated
  2. customThe flask was then fitted with a condenser
  3. customAn orange precipitate formed
  4. customThe flask was removed from the heat
  5. temperaturecooled
  6. temperaturechilled in ice
  7. waitAfter 1 hour
  8. filtrationthe reddish precipitate was filtered off
  9. additionThe filtrate was poured into 300 ml diethyl ether
  10. stirringstirred for 2 hors
  11. filtrationThe resulting yellow-orange powder was filtered
  12. washwashed with ether
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-129ff1a456fc41a798c0e43b5d6a09b0
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900652

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