Sulfuric Acid → HCID 20553480, compound

HRID 1446902Notes

Reaction equation

HRID 1446902 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]([C:20]=1[Cl:21])=[N:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([O:23][CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[C:16]=1[Cl:22])[CH:11]=2)[CH3:2].S(=O)(=O)(O)O.[N+:38]([O-])([O-:40])=[O:39].[K+].[OH-].[Na+]>>[CH2:27]([N:26]([CH2:29][CH3:30])[CH2:25][CH2:24][O:23][C:15]1[C:14]([N+:38]([O-:40])=[O:39])=[CH:13][C:12]2[C:17]([C:16]=1[Cl:22])=[N:18][C:19]1[C:10](=[CH:9][CH:8]=[C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:31][CH3:32])[C:20]=1[Cl:21])[CH:11]=2)[CH3:28]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 20553463HCID 20553463, compound

Product 1

HCID 20553480HCID 20553480, compound

Conditions

Temperature
0 °C

Procedure

A 119.5 mg. portion of 3,6-bis(2-diethylaminoethoxy)-4,5-dichloroacridine is dissolved in one ml. of concentrated sulfuric acid. The solution is cooled in an ice bath and 60 mg. of potassium nitrate are added. The mixture is stirred at 0° C. for one hour, then at room temperature for 20 hours, poured into 20 ml. of ice water and the pH adjusted to 11.5 with 5 N sodium hydroxide. The mixture is then extracted three times with dichloromethane. The extracts are combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to a black gum. This gum is slurried in 25 ml. of boiling hexane and filtered. The filtrate is concentrated to 10 ml. and cooled in an ice bath. The crystals are collected and dried in vacuo, giving 54 mg. of the desired product, m.p. 100°-102° C.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. waitat room temperature for 20 hours
  3. additionpoured into 20 ml
  4. extractionThe mixture is then extracted three times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a black gum
  8. filtrationof boiling hexane and filtered
  9. concentrationThe filtrate is concentrated to 10 ml
  10. temperatureand cooled in an ice bath
  11. customThe crystals are collected
  12. customdried in vacuo
  13. customgiving 54 mg

Sources & evidence

ORD record
ord-02b7414d30244e74860fa03f249a32bc
Source dataset
uspto-grants-1982_02
Patent number
US04314061

Reaction notes

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