Ammonium Hydroxide → 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione

HRID 2170142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170142
C([O:3][C:4]([NH:6][N:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]1[C:18]([O:20]C)=O)=O)C.[OH-].[NH4+:23]>>[C:12]1([C:9]2[CH:10]=[CH:11][N:7]3[C:8]=2[C:18](=[O:20])[NH:23][C:4](=[O:3])[NH:6]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 14923Ammonium HydroxideHCID 90386155methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 903861165-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dioneAusbeute 38,1 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate (1.00 g, 3.47 mmol) was taken in a pressure tube and ammonium hydroxide (30%, 67.5 mL, 1.73 mol) was added and sealed. The reaction mixture was stirred at 110° C. for 30 h and transferred to a round bottomed flask and concentrated under reduced pressure. Toluene was added to it and azeotroped to remove trace amount of water (3 times). Then residue obtained was triturated with ethyl acetate (50×2 mL) to afford 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione (0.300 g, 38.1%). LCMS Condition B-39: retention time 1.49 min, [M+1]=228.0.

Aufarbeitung

  1. customsealed
  2. customtransferred to a round bottomed flask
  3. concentrationconcentrated under reduced pressure
  4. additionToluene was added to it
  5. customazeotroped
  6. customto remove trace amount of water (3 times)
  7. customThen residue obtained
  8. customwas triturated with ethyl acetate (50×2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-09ac7eee98a24cecbfeb1f9146261945
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050345B2

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