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 2398523Notes

Reaction equation

HRID 2398523 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1,3-Diethyl-1,2-dihydro-2-methyleneimidazo[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 with 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.

Workup

  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 with 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

Sources & evidence

ORD record
ord-ca817ef18eae4636a2b3a28121634f70
Source dataset
uspto-grants-1977_05
Patent number
US04025349

Reaction notes

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