Dimethyl Sulfoxide → HCID 135783950, compound

HRID 1578521Notes

Reaction equation

HRID 1578521 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.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24].CS(C)=O>C(Cl)(Cl)Cl>[CH2:23]([N:25]([CH2:26][CH3:27])[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)[CH3:24]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8021DiethylamineHCID 135783957HCID 135783957, compound

Product 1

HCID 135783950HCID 135783950, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.0 grams of 6-(3-chloropropoxy)-1-phenazinol 5,10-dioxide and 25ml of diethylamine were placed in a flask. To this was added 50ml of dimethylsulfoxide. The reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was then diluted with 400ml CHCl3 and washed first with very dilute acetic acid and then with water until the water washes were neutral. The CHCl3 layer was extracted with 10 percent aqueous HCl. The combined HCl extracts were neutralized with sodium carbonate and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was slurried with ether/pentane (1:1) and filtered to yield red crystals of 6-(3-diethylaminopropoxy)-1-phenazinol 5,10-dioxide, m.p. 78°-80° (dec.).

Workup

  1. washwashed first with very dilute acetic acid
  2. extractionThe CHCl3 layer was extracted with 10 percent aqueous HCl
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered

Sources & evidence

ORD record
ord-35c3a3e328cc43658dde360295bf2897
Source dataset
uspto-grants-1976_02
Patent number
US03937707

Reaction notes

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