Dimethylamine → HCID 135783949, compound

HRID 1578520Notes

Reaction equation

HRID 1578520 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:7]=1[N+:8]([O-:22])=[C:9]1[C:14](=[N+:15]2[O-:20])[C:13]([OH:21])=[CH:12][CH:11]=[CH:10]1.[CH3:23][NH:24][CH3:25]>C(=O)=O.CC(C)=O>[CH3:23][N:24]([CH3:25])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:7]=1[N+:8]([O-:22])=[C:9]1[C:14](=[N+:15]2[O-:20])[C:13]([OH:21])=[CH:12][CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 135783957HCID 135783957, compound

Product 1

HCID 135783949HCID 135783949, compound

Reagents, catalysts & solvents 1

HCID 18522661Acetone cardiceSolvent

Procedure

Into a sealed tube was placed 2.0 grams of 6-(3-chloropropoxy)-1-phenazinol 5,10-dioxide. The tube was cooled in dry-ice-acetone and 80 ml of dimethylamine was condensed into the tube. The tube was sealed and shaken at room temperature for 70 hours. The tube was then opened and excess dimethylamine allowed to evaporate at room temperature. The residue was dissolved in CHCl3 solution, was washed with water and was then extracted with 3 × 150ml 10 percent aqueous HCl. The combined acid extracts were made basic with sodium carbonate, extracted with CHCl 3 and the combined CHCl3 extracts were washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was recrystallized from acetone/ether to yield 6-(3-dimethylaminopropoxy)-1-phenazinol 5,10-dioxide, mp. 103°C (dec.).

Workup

  1. customInto a sealed tube was placed
  2. customcondensed into the tube
  3. customThe tube was sealed
  4. customto evaporate at room temperature
  5. dissolutionThe residue was dissolved in CHCl3 solution
  6. washwas washed with water
  7. extractionwas then extracted with 3 × 150ml 10 percent aqueous HCl
  8. extractionextracted with CHCl 3
  9. washthe combined CHCl3 extracts were washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was recrystallized from acetone/ether

Sources & evidence

ORD record
ord-2b89bfbe913b46bd8272772d741b2534
Source dataset
uspto-grants-1976_02
Patent number
US03937707

Reaction notes

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