Dimethyl Sulfoxide → HCID 21519479, compound

HRID 1283221Notes

Reaction equation

HRID 1283221 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:17])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][Cl:25])[CH3:20].[OH-].[Na+].CS(C)=O>O>[ClH:25].[ClH:25].[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH3:27])[CH2:19][CH3:20])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1)[CH3:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 67762,6-DihydroxyanthraquinoneHCID 14798Sodium HydroxideHCID 669183-Chloropropyl(diethyl)amine

Product 1

HCID 21519479HCID 21519479, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12 g. (0.05 mole) of 2,6-dihydroxyanthraquinone, 16.5 g (0.11 mole) of 3-diethylaminopropyl chloride, 48 ml. of 10% sodium hydroxide solution, and 100 ml. of dimethylsulfoxide was stirred and heated on a steam bath for two hours. When cool, the mixture was poured into about 500 ml. of water. The solid which precipitated was filtered with suction and washed with water. The crude wet solid was dissolved in chloroform. This solution was dried over anhydrous magnesium sulfate, filtered, and the filtrate acidified to Congo Red with ethereal hydrogen chloride. After dilution with anhydrous ether, the yellow solid was filtered and dried. After two recrystallizations from 95% ethanol, the dihydrochloride (a hydrate) melted with decomposition at 273.5°-274.5°C; γmax (H2O) 274, E1cm1% 761.

Workup

  1. additionA mixture of 12 g
  2. temperatureheated on a steam bath for two hours
  3. temperatureWhen cool
  4. additionthe mixture was poured into about 500 ml
  5. customThe solid which precipitated
  6. filtrationwas filtered with suction
  7. washwashed with water
  8. dissolutionThe crude wet solid was dissolved in chloroform
  9. dry with materialThis solution was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. filtrationAfter dilution with anhydrous ether, the yellow solid was filtered
  12. customdried
  13. customAfter two recrystallizations from 95% ethanol
  14. custommelted with decomposition at 273.5°-274.5°C

Sources & evidence

ORD record
ord-336a0f0eb80f488eb69088d21ebcd70f
Source dataset
uspto-grants-1976_08
Patent number
US03974186

Reaction notes

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