Diethyl Ether → 1,3-Dimethyl-2-[2-(1-phenyl-3-indazolyl)vinyl]1H-imidazo[4,5-b]pyrazinium p-toluenesulfonate

HRID 436202Notes

Reaction equation

HRID 436202 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][NH+:13]1[C:17]2=[N:18][CH:19]=[CH:20][N:21]=[C:16]2[N:15]([CH3:22])[CH:14]1[CH3:23].[CH:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:27]=1)=O.CCOCC>C(OC(=O)C)(=O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH3:22][NH+:15]1[C:16]2=[N:21][CH:20]=[CH:19][N:18]=[C:17]2[N:13]([CH3:12])[CH:14]1[CH:23]=[CH:24][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:27]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 214547813-Formyl-1-phenylindazoleHCID 214547841,2,3-trimethyl-1H-imidazo[4,5-b]-pyrazinium p-toluenesulfonate

Product 1

HCID 737919641,3-Dimethyl-2-[2-(1-phenyl-3-indazolyl)vinyl]1H-imidazo[4,5-b]pyrazinium p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 1,2,3-trimethyl-1H-imidazo[4,5-b]-pyrazinium p-toluenesulfonate (1.67 g, 0.050 mole) and 3-formyl-1-phenylindazole (1.11 g, 0.050 mole) is heated together in acetic anhydride (15 ml) at reflux for 30 minutes. After chilling, ether (500 ml) is added and the solid which separates is filtered off and dried. Yield 1.92 g, (72%). After recrystallization from water the yield of dye is 0.55 g (41%).

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureAfter chilling
  3. filtrationthe solid which separates is filtered off
  4. customdried
  5. customAfter recrystallization from water the yield of dye

Sources & evidence

ORD record
ord-6530c8186d724382beb1e04e3647c743
Source dataset
uspto-grants-1977_02
Patent number
US04007170

Reaction notes

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