Ethanol → 4-(4'-Dimethylaminophenyl)-2,6-diphenylthiapyrylium 4-(4'-dimethylaminophenylazo) benzenesulphonate

HRID 1282978Notes

Reaction equation

HRID 1282978 reaction equation
[Cl-].[CH3:2][N:3]([CH3:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S+:13]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=2)=[CH:6][CH:5]=1.C(O)C.[CH3:32][N:33]([C:35]1[CH:36]=[CH:37][C:38]([N:41]=[N:42][C:43]2[CH:44]=[CH:45][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:47][CH:48]=2)=[CH:39][CH:40]=1)[CH3:34]>O>[CH3:32][N:33]([CH3:34])[C:35]1[CH:36]=[CH:37][C:38]([N:41]=[N:42][C:43]2[CH:48]=[CH:47][C:46]([S:49]([O-:52])(=[O:51])=[O:50])=[CH:45][CH:44]=2)=[CH:39][CH:40]=1.[CH3:2][N:3]([CH3:28])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S+:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 178482633HCID 178482633, compound

Product 1

HCID 1784826354-(4'-Dimethylaminophenyl)-2,6-diphenylthiapyrylium 4-(4'-dimethylaminophenylazo) benzenesulphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-(4'-dimethylaminophenyl)-2,6-diphenylthiapyrylium chloride, 8.07 g, in a hot mixture of water, 400 mls, and ethanol, 100 mls, is added a solution of Methyl Orange, E. K. 432, 6.8 g, in hot water, 200 mls, with stirring. The mixture is stirred for 10 minutes and then is cooled and filtered, the filtrate being orange-red in color. The solid product is taken up in boiling nitromethane, filtered hot, evaporated down somewhat, and diluted with ethanol. The solid which crystallizes out overnight is filtered off. Yield: 9.3 g. of product having structural formula II noted above and exhibiting light absorption maxima (when dissolved in ethanol) at 582 and 427 nm.

Workup

  1. temperatureis cooled
  2. filtrationfiltered
  3. filtrationfiltered hot
  4. customevaporated down somewhat
  5. additiondiluted with ethanol
  6. customThe solid which crystallizes out overnight
  7. filtrationis filtered off
  8. customlight absorption maxima (when dissolved in ethanol) at 582 and 427 nm

Sources & evidence

ORD record
ord-f9bf98fd4d1341e29d0bd2b9c74b8563
Source dataset
uspto-grants-1976_08
Patent number
US03973962

Reaction notes

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