Ethanol → HCID 178482634, compound

HRID 1282981Notes

Reaction equation

HRID 1282981 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]([CH3:51])[C:34]1[CH:39]=[CH:38][C:37]([N:40]=[N:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([O-:48])=[O:47])=[CH:44][CH:43]=2)=[CH:36][CH:35]=1.[Na+]>O>[CH3:32][N:33]([CH3:51])[C:34]1[CH:35]=[CH:36][C:37]([N:40]=[N:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([O-:48])=[O:47])=[CH:44][CH:43]=2)=[CH:38][CH:39]=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 23674498Benzoic acid, 4-[[4-(dimethylamino)phenyl]azo]-, sodium saltHCID 178482633HCID 178482633, compound

Product 1

HCID 178482634HCID 178482634, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a hot solution composed of 4.04 g. 4-(4-dimethylaminophenyl)-2,6-diphenylthiapyrylium chloride, 200 mls. water, and 50 mls. ethanol, was added in one portion a solution of sodium 4-(4-dimethylaminophenylazo)benzoate, 3.0 g., in hot water, 150 mls. There was immediate formation of a fine, dark-brown precipitate. The reaction mixture was quickly chilled in ice, and then filtered. The filtrate was a clear, deep orange. The solid was washed with cold water until the washings were only weakly orange. The solid was sucked dry and then a portion of it was dissolved in boiling acetonitrile, filtered hot, and evaporated down. The crystalline solid that came down on cooling the concentrated solution was filtered off and dried in vacuo. This solid was found to contain the above-noted thiapyrylium-azo dye salt.

Workup

  1. temperatureThe reaction mixture was quickly chilled in ice
  2. filtrationfiltered
  3. washThe solid was washed with cold water until the washings
  4. customThe solid was sucked dry
  5. dissolutiona portion of it was dissolved
  6. filtrationfiltered hot
  7. customevaporated down
  8. temperatureon cooling the concentrated solution
  9. filtrationwas filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d5846a98ca5d46b092763da42d65d79d
Source dataset
uspto-grants-1976_08
Patent number
US03973962

Reaction notes

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