3-Nitrophenylboronic Acid → HCID 178514280, Verbindung

HRID 343991

Reaktionsgleichung

Reaktionsgleichung von HRID 343991
[NH2:1][NH:2][C:3]([NH:5][NH2:6])=[S:4].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:20][CH3:21])C(O)=O)=[CH:12][CH:11]=1)([O-:9])=[O:8].[N+]([C:25]1C=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[CH2:21][CH2:20][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 16773-Nitrophenylboronic AcidHCID 240472-(4-Nitrophenyl)butyric acidHCID 2724189Thiocarbohydrazide

Produkt 1

HCID 178514280HCID 178514280, VerbindungAusbeute 647,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 4.9 g (47 mmol) of thiocarbohydrazide and 9.8 g (47 mmol) of 4-nitrophenylbutanoic 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. The reaction was cooled and the reaction mixture was allowed to settle. The supernatant liquid was decanted. To the residual solid was added 50 mL of acetonitrile. The mixture was stirred for 30 minutes. The solid was collected, rinsed with 10 mL of acetonitrile and dried in vacuo to yield 8.5 g (65.4%) of the desired product as a white sandy material. All the analytical data confirmed the assigned structure.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe reaction was cooled
  4. customThe supernatant liquid was decanted
  5. additionTo the residual solid was added 50 mL of acetonitrile
  6. customThe solid was collected
  7. washrinsed with 10 mL of acetonitrile
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-61054827c0584a55a09e22bc7caebfdd
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864042

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