Benzylamine → 1-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-2-ol

HRID 1181155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181155
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5](Br)[N:4]([CH2:11][CH:12]([OH:14])[CH3:13])[N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OC(C)C)(C)C>CCO>[CH2:15]([NH:22][C:5]1[N:4]([CH2:11][CH:12]([OH:14])[CH3:13])[N:3]=[C:2]([Br:1])[C:6]=1[N+:7]([O-:9])=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 7914Diisopropyl EtherHCID 130072261-(3,5-Dibromo-4-nitropyrazol-1-yl)propan-2-ol

Produkt 1

HCID 130072301-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-2-olAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(3,5-dibromo-4-nitropyrazol-1-yl)propan-2-ol (3-3) (22 g, 666 mmol), EtOH (300 ml) and benzylamine (102 g, 936 mmol) was refluxed for 1.5 hours. The reaction medium was concentrated to the maximum under reduced pressure. DCM (100 ml) was added to the residue. The organic phase was washed with dilute acid (5×50 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The brown oil obtained was treated with diisopropyl ether at 0° C. to give the 1-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-2-ol (13.7 g, 58%) in the form of a yellow solid.

Aufarbeitung

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe reaction medium was concentrated to the maximum under reduced pressure
  3. additionDCM (100 ml) was added to the residue
  4. washThe organic phase was washed
  5. additionwith dilute acid (5×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customThe brown oil obtained

Quellen und Nachweise

ORD-Eintrag
ord-764bc32027614408a326cdf66aad928f
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285136B2

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