Dimethyl Sulfate → HCID 21331925, compound

HRID 1390926Notes

Reaction equation

HRID 1390926 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])[C:5]([Cl:23])=[C:4]([Cl:24])[N:3]=1.[C:25](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([N:9]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([F:22])([F:20])[F:21])[CH3:25])[C:5]([Cl:23])=[C:4]([Cl:24])[N:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 21331926HCID 21331926, compound

Product 1

HCID 21331925HCID 21331925, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(2,3,5,6-Tetrachloro-4-pyridyl)-N-(4-nitro-2-trifluoromethylphenyl)amine (2.0 grams; 0.005 mole), 30 ml. of acetone, 6.0 grams of sodium carbonate and 6 ml. of dimethyl sulfate were mixed and refluxed. After 2 hours, TLC showed no evidence of product. After 8 hours, TLC showed evidence of some product formation. After about sixteen hours, the reaction mixture was quenched by adding water, heating for one hour, and then allowing to cool. Product precipitated and was separated by filtration. It was purified by passing it through a silica gel column with toluene as eluent. Yield was 0.31 gram, m.p. 152°-155° C. Elemental analysis showed

Workup

  1. temperaturerefluxed
  2. waitAfter 8 hours
  3. waitAfter about sixteen hours
  4. customthe reaction mixture was quenched
  5. additionby adding water
  6. temperatureheating for one hour
  7. temperatureto cool
  8. customProduct precipitated
  9. customwas separated by filtration
  10. customIt was purified

Sources & evidence

ORD record
ord-7590805d92ad4b57a7ea6d4680eeb7e0
Source dataset
uspto-grants-1979_02
Patent number
US04140778

Reaction notes

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