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Triethylamine → Pyrrolo(1,2-a)(1,4)diazepine

HRID 439980
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 439980
O1[C:5]2[NH:6][CH2:7][C:8]3[N:9]([CH:11]=[CH:12][CH:13]=3)[CH2:10][C:4]=2C=C1.C(N(CC)CC)C.[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O>C(Cl)Cl.C(OCC)(=O)C>[CH:7]1[C:8]2[N:9]([CH:11]=[CH:12][CH:13]=2)[CH2:10][CH:4]=[CH:5][N:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 218369669,10-Dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine

Produkt 1

HCID 45087533Pyrrolo(1,2-a)(1,4)diazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

To a solution of 1.0 mmol of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine in 10 ml of methylene chloride under argon is added 1.5 mmol of triethylamine followed by ice bath cooling. A solution of 1.1 mmol of 4-nitrobenzoyl chloride in 5 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture is stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 1N HCl, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give desired product as a solid.

Aufarbeitung

  1. customfollowed by ice bath
  2. temperaturecooling
  3. additionaddition
  4. customthe ice bath is removed
  5. customThe volatiles are removed in vacuo
  6. customto give a residue which
  7. washThe solution is washed with water, 1N HCl, NaHCO3, and brine
  8. dry with materialThe reaction mixture is dried with Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto give a solid which
  12. customis purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c09f98063a2f40489166940e1c21177a
Quelldatensatz
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05516774

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