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Triethylamine → 5-[(1,3-diethyl-1,3-dihydro-2H-imidazo[4,5-b]quinoxalin-2-ylidene)ethenylidene]-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

HRID 1679499
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Reaktionsgleichung

Reaktionsgleichung von HRID 1679499
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([N:15]=[C:6]2[N:5]([CH2:16][CH3:17])[C:4]1=[CH2:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:19]([N:21]1[C:28](=[O:29])[CH2:27][C:25](=[O:26])[N:24]([CH2:30][CH3:31])[C:22]1=[S:23])[CH3:20].[C:32](Br)(Br)(Br)Br.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:30]([N:24]1[C:25](=[O:26])[C:27](=[C:32]=[C:18]=[C:4]2[N:5]([CH2:16][CH3:17])[C:6]3=[N:15][C:14]4[C:9]([N:8]=[C:7]3[N:3]2[CH2:1][CH3:2])=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:28](=[O:29])[N:21]([CH2:19][CH3:20])[C:22]1=[S:23])[CH3:31]
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 788901,3-Diethyl-2-thiobarbituric acidHCID 198738891,3-diethyl-2-methylidene-2,3-dihydro-1H-imidazo[4,5-b]quinoxaline

Produkt 1

HCID 867347755-[(1,3-diethyl-1,3-dihydro-2H-imidazo[4,5-b]quinoxalin-2-ylidene)ethenylidene]-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 1,3-Diethyl-1,2-dihydro-2methyleneimidazo[4,5-b]quinoxaline (6.0 g, 0.025 mol), 1,3-diethyl-2-thiobarbituric acid (5.0 g, 0.025 mol) and carbon tetrabromide (8.3 g, 0.025 mol) in benzene (60 ml) is warmed to 50°-55°, at which point an exothermic reaction occurs, with separation of solid. The mixture is allowed to cool, then filtered. The filtrate is evaporated to dryness, the residue treated wth methanol (50 ml), and the solid dye collected. Treatment of the filtrate with triethylamine (5 ml) yields a further portion of dye. The dye is purified by precipitation from chloroform solution by addition of methanol. The yield of purified dye is 0.50 g, mp indistinct. The yield can be improved by using the quaternary salt and conducting the reaction in the presence of triethylamine.

Aufarbeitung

  1. customan exothermic reaction
  2. customoccurs, with separation of solid
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness
  6. additionthe residue treated wth methanol (50 ml)
  7. customthe solid dye collected
  8. customTreatment of the filtrate with triethylamine (5 ml) yields a further portion of dye
  9. customThe dye is purified by precipitation from chloroform solution by addition of methanol
  10. customThe yield can

Quellen und Nachweise

ORD-Eintrag
ord-5745288d7d9b4db39d26f2ca137a60a0
Quelldatensatz
uspto-grants-1978_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04080496

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