Phenazine → HCID 178503009, compound

HRID 64770

Reaction equation

HRID 64770 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.[N+]([C:18]1C=CC=CC=1)([O-])=O.[CH3:24][O:25][S:26]([O:29]C)(=[O:28])=[O:27]>>[CH3:24][O:25][S:26]([O-:29])(=[O:28])=[O:27].[CH3:18][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[N:13]=[C:14]1[C:5]([CH:4]=[CH:3][CH:2]=[CH:1]1)=[NH+:6]2

Participants

4

Reactant 3

HCID 4757PhenazineHCID 6497Dimethyl SulfateHCID 7416Nitrobenzene

Product 1

HCID 178503009HCID 178503009, compoundYield 67%

Conditions

Temperature
100 °C

Procedure

1.76 g (0.011 mol) of phenazine and 33.5 ml of dry nitrobenzene are heated to boiling, cooled to 100° C., added with 12.2 g (0.011 mol) of freshly distilled dimethylsulphate and heated for 7 minutes at the temperature of 100° C. Then the reaction mixture is cooled with ice and allowed to stand for 48 hours at the temperature of 4° C. in a refrigerator. The formed precipitate is filtered off, washed with 30 ml of ethyl ether and recrystallized from 15 ml of ethanol. 2.0 g of 9-methylphenazinium methylsulphate (67%) are thus obtained in the form of yellowish crystals melting at 155°-157° C.

Workup

  1. temperatureheated for 7 minutes at the temperature of 100° C
  2. temperatureThen the reaction mixture is cooled with ice
  3. filtrationThe formed precipitate is filtered off
  4. washwashed with 30 ml of ethyl ether
  5. customrecrystallized from 15 ml of ethanol

Sources & evidence

ORD record
ord-4131871b38af4fd5ae319ab0057b9ff1
Source dataset
uspto-grants-1986_09
Patent number
US04610767

Linked notes

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