3-Nitrophenylboronic Acid → 4-Amino-3-[3-(dodecylsulfonyl)propyl]-5-mercapto-[1,2,4]triazole

HRID 343990

Reaktionsgleichung

Reaktionsgleichung von HRID 343990
[NH2:1][NH:2][C:3]([NH:5][NH2:6])=[S:4].[CH2:7]([S:19]([CH2:22][CH2:23][CH2:24][C:25](O)=O)(=[O:21])=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N+](C1C=C(B(O)O)C=CC=1)([O-])=O>C1(C)C=CC=CC=1>[NH2:6][N:5]1[C:3]([SH:4])=[N:2][N:1]=[C:25]1[CH2:24][CH2:23][CH2:22][S:19]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:20])=[O:21]

Komponenten

5

Edukt 3

HCID 16773-Nitrophenylboronic AcidHCID 2724189ThiocarbohydrazideHCID 11001756Butanoic acid, 4-(dodecylsulfonyl)-

Produkt 1

HCID 1784433204-Amino-3-[3-(dodecylsulfonyl)propyl]-5-mercapto-[1,2,4]triazoleAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 4.9 g (47 mmol) of thiocarbohydrazide and 15 g (47 mmol) of 4-(dodecylsulfonyl)butanoic acid in 30 ml of toluene was added 0.8 g (4.7 mmol) of 3-nitrobenzeneboronic acid. The mixture was heated at reflux for 24 hr. Upon cooling, the thick precipitate was collected, rinsed with a small amount of acetonitrile (10 ml), dried in vacuo to yield 16 g (87.4%) of the desired product as a white solid. All of the analytical data confirmed the assigned structure.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hr
  3. temperatureUpon cooling
  4. customthe thick precipitate was collected
  5. washrinsed with a small amount of acetonitrile (10 ml)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4018f3024dfc4ad7a6b912475ebb76af
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864042

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