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

HRID 49813Notes

Reaction equation

HRID 49813 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-882fde17102740048fe6d4b5925eed88
Source dataset
uspto-grants-2004_03
Patent number
US06710044B2

Reaction notes

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