Dimethyl Sulfate → 1-Methyl-3-(3-nitrophenyl)pyridinium methyl sulfate

HRID 324730Notes

Reaction equation

HRID 324730 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[S:16]([O:21]C)([O:19][CH3:20])(=[O:18])=[O:17]>C(OCC)C>[CH3:20][O:19][S:16]([O-:21])(=[O:18])=[O:17].[CH3:20][N+:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 6497Dimethyl Sulfate2×HCID 121813273-(3-Nitrophenyl)pyridine

Product 1

HCID 227418351-Methyl-3-(3-nitrophenyl)pyridinium methyl sulfateYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-(3-nitrophenyl)pyridine (50 g, 0.25 mol) was added portion-wise with stirring to dimethyl sulfate (125 ml). The mixture was stirred at ambient temperature for 24 hours, during which time additional dimethyl sulfate was added (2×50 ml). At the end of the reaction diethyl ether (400 ml) was added, and the mixture was stirred in the cold for 2 hours. The precipitate was filtered off and washed several times with diethyl ether. Finally, the precipitate was stirred in pyridine (100 ml) at 45° C. for 30 min. THF (250 ml) was added. Stirring was continued for additionally 30 min whereafter the product was filtered off, washed with diethyl ether and dried to yield 1-methyl-3-(3-nitrophenyl)pyridinium methyl sulfate (66.6 g, 82%).

Workup

  1. additionwas added (2×50 ml)
  2. additionwas added
  3. filtrationThe precipitate was filtered off
  4. washwashed several times with diethyl ether
  5. stirringFinally, the precipitate was stirred in pyridine (100 ml) at 45° C. for 30 min
  6. additionTHF (250 ml) was added
  7. stirringStirring
  8. waitwas continued for additionally 30 min whereafter the product
  9. filtrationwas filtered off
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-a689a3f577854ad0adf11e2116d74f2c
Source dataset
uspto-grants-2001_04
Patent number
US06218547B1

Reaction notes

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