Hydrochloric Acid → HCID 86733804, compound

HRID 1282987Notes

Reaction equation

HRID 1282987 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:12]=O)=[CH:6][CH:5]=1.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH3:35])([CH3:34])[C:26]1=[CH2:36]>C(O)(=O)C>[Cl-:1].[CH3:2][N:3]([CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:12]=[CH:36][CH:26]2[C:27]([CH3:35])([CH3:34])[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH+:25]2[CH3:24])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 872182-Propenal, 3,3-bis[4-(dimethylamino)phenyl]-

Product 1

HCID 86733804HCID 86733804, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a suitable container equipped with an air condenser and a drying tube to exclude atmospheric moisture and heated by a steam bath, are placed 50 parts glacial acetic acid, 2 parts of concentrated hydrochloric acid, 7.07 parts of 3,3-bis(4-dimethylaminophenyl)acrolein (0.024 moles) and 4.16 parts of 1,3,3-trimethyl-2-methylene-indoline (0.024 moles). The mixture is heated for 18 hours during which time it takes on a deep blue coloration. The solution is concentrated to about one-half its initial volume, diluted to 600 parts by volume with water and salted out with a mixture of sodium chloride and sodium acetate. After filtering and drying, the solid is extracted with chloroform in a Soxhlet extractor to remove salt and the chloroform concentrate evaporated to yield 11.7 parts of green-grey microcrystals of 2-(4,4-bis-(4-dimethylaminophenyl)butadienyl)-1,3,3-trimethylindolinium chloride.

Workup

  1. customIn a suitable container equipped with an air condenser and a drying tube
  2. temperatureheated by a steam bath
  3. temperatureThe mixture is heated for 18 hours during which time it
  4. concentrationThe solution is concentrated to about one-half its initial volume
  5. additiondiluted to 600 parts by volume with water
  6. additionsalted out with a mixture of sodium chloride and sodium acetate
  7. filtrationAfter filtering
  8. customdrying
  9. extractionthe solid is extracted with chloroform in a Soxhlet extractor
  10. customto remove salt
  11. concentrationthe chloroform concentrate
  12. customevaporated

Sources & evidence

ORD record
ord-37b2e8c7fc0f4014825f4459c707ac45
Source dataset
uspto-grants-1976_08
Patent number
US03974147

Reaction notes

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