Water → 1,3-Diethyl-5-{bis[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)methyl]methylene}-2-thiobarbituric acid

HRID 2399016Notes

Reaction equation

HRID 2399016 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([N+:8]1[C:12]2=[N:13][C:14]3[C:19]([N:20]=[C:11]2[N:10]([CH2:21][CH3:22])[C:9]=1[C:23]#[C:24][CH:25]=[C:26]1[N:38]([CH2:39][CH3:40])[C:29]2=[N:30][C:31]4[C:36]([N:37]=[C:28]2[N:27]1[CH2:41][CH3:42])=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:7].[CH2:43]([N:45]1[C:52](=[O:53])[CH2:51][C:49](=[O:50])[N:48]([CH2:54][CH3:55])[C:46]1=[S:47])[CH3:44].C(N(CC)CC)C.O>CN(C)C=O>[CH2:54]([N:48]1[C:49](=[O:50])[C:51](=[C:24]([CH:25]=[C:26]2[N:27]([CH2:41][CH3:42])[C:28]3=[N:37][C:36]4[C:31]([N:30]=[C:29]3[N:38]2[CH2:39][CH3:40])=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:23]=[C:9]2[N:10]([CH2:21][CH3:22])[C:11]3=[N:20][C:19]4[C:14]([N:13]=[C:12]3[N:8]2[CH2:6][CH3:7])=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:52](=[O:53])[N:45]([CH2:43][CH3:44])[C:46]1=[S:47])[CH3:55]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 788901,3-Diethyl-2-thiobarbituric acidHCID 867347981,3-diethyl-2-[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)-1-propynyl]imidazo[4,5-b]quinoxalinium perchlorate

Product 1

HCID 203629651,3-Diethyl-5-{bis[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)methyl]methylene}-2-thiobarbituric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3-diethyl-2-[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)-1-propynyl]imidazo[4,5-b]quinoxalinium perchlorate) 0.33 g, 0.0005 mol) of Example 1, 1,3-diethyl-2-thiobarbituric acid (0.11 g, 0.0005 mol) and triethylamine (0.10 g, 0.001 mol) in dimethylformamide (5 ml), is heated at reflux for 30 seconds. After cooling the solution is diluted to 20 ml. with water. The dye is collected and washed with water. After recrystallization from acetonitrile, the yield of purified dye is 0.27 g (79%) - mp. indistinct.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 seconds
  3. temperatureAfter cooling the solution
  4. additionis diluted to 20 ml
  5. customThe dye is collected
  6. washwashed with water
  7. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-d6d913b26305447bad7825424cc6a030
Source dataset
uspto-grants-1977_05
Patent number
US04026884

Reaction notes

Loading…