Dimethyl Sulfate → HCID 54075718, compound

HRID 1156838Notes

Reaction equation

HRID 1156838 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[N:4]([C:10]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=[O:11])[CH2:5][C:6](=[N:8][OH:9])[CH3:7].S(OC)(O[CH3:26])(=O)=O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.[OH-].[Na+].C(Cl)Cl>[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[N:4]([C:10]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=[O:11])[CH2:5][C:6](=[N:8][O:9][CH3:26])[CH3:7]

Participants

6

Reactant 2

HCID 6497Dimethyl SulfateHCID 73682687HCID 73682687, compound

Product 1

HCID 54075718HCID 54075718, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

7 g (0.024 mol) of 2,6-dimethyl-N-(2-furoyl)-N-(2-hydroxyimino-prop-1-yl)-aniline (Example 3) and 0.5 g of triethylbenzylammonium chloride were dissolved in a two-phase mixture of 30 ml of 50% strength sodium hydroxide solution and 100 ml of methylene chloride, and 3.7 g (0.03 mol) of dimethyl sulphate were added, while stirring vigorously. During this addition, the temperature rose from about 20° C. to about 32° C. After stirring the mixture at room temperature for 12 hours, the phases were separated. The organic phase was washed again with water, dried over sodium sulphate and concentrated. The resulting dark oil was distilled in a bulb tube apparatus (boiling point 170° C./0.1 mm Hg). The product (2.3 g) which had crystallized out was recrystallized from petroleum ether. 1.4 g (20% of theory) of 2,6-dimethyl-N-(2-furoyl)-N-(2-methoxyimino-prop-1-yl)-aniline of melting point 108°-109° C. were obtained.

Workup

  1. additionwere added
  2. additionDuring this addition
  3. customrose from about 20° C. to about 32° C
  4. stirringAfter stirring the mixture at room temperature for 12 hours
  5. customthe phases were separated
  6. washThe organic phase was washed again with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationThe resulting dark oil was distilled in a bulb tube apparatus (boiling point 170° C./0.1 mm Hg)
  10. customThe product (2.3 g) which had crystallized out
  11. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-7a48b672c6fc43a799170130a697276f
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

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