Phenazine → Phenazine Methosulfate

HRID 279726

Reaction equation

HRID 279726 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([N:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[S:15]([O:20]C)([O:18][CH3:19])(=[O:17])=[O:16]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:19][N+:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[N:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2.[CH3:19][O:18][S:15]([O-:20])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 4757PhenazineHCID 6497Dimethyl Sulfate

Product 1

HCID 9285Phenazine MethosulfateYield 53.8%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

5-methyl phenazinium methosulfate was prepared by quaternizing 36.0 g (200 mmoles) of phenazine with 25.2 g (200 mmoles) of dimethyl sulfate in 300 ml of nitrobenzene in a 500 ml 3-neck, round-bottom flask. The mixture was gradually heated to 80 degrees Celsius and then held at that temperature for 2 hours. After cooling, the methosulfate salt was filtered off and washed with ethanol for a 53.8% yield.

Workup

  1. temperatureThe mixture was gradually heated to 80 degrees Celsius
  2. temperatureAfter cooling
  3. filtrationthe methosulfate salt was filtered off
  4. washwashed with ethanol for a 53.8% yield

Sources & evidence

ORD record
ord-90dbc58d40c14fb094b831add147b011
Source dataset
uspto-grants-2002_03
Patent number
US06362914B1

Linked notes

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