Dimethyl Sulfate → HCID 20311579, compound

HRID 442032Notes

Reaction equation

HRID 442032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11](=[O:13])[N:10]=[C:9]2[NH:14][CH3:15])=[CH:4][CH:3]=1.S(OC)(O[CH3:20])(=O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C:11](=[O:13])[N:10]([CH3:20])[C:9]2=[N:14][CH3:15])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 178482453HCID 178482453, compound

Product 1

HCID 20311579HCID 20311579, compound

Procedure

3 g. of 1-(p-chlorophenyl)-2-methylamino-4-oxo-2-imidazoline and 9 ml. dimethyl sulfate were heated slowly to 120° C. with stirring. The reaction mixture, cooled to room temperature, was filtered. The clear filtrate diluted with 150 ml. H2O was extracted once with 200 ml. ether. The aqueous layer was separated and made basic with 5N NaOH and cooling. The precipitate was filtered and recrystallized once with acetonitrile. Thin-layer chromatography gave a single spot. The yield of product, m.p. 150°-152° C., was 1.6 g. (50%).

Workup

  1. filtrationwas filtered
  2. additionThe clear filtrate diluted with 150 ml
  3. extractionH2O was extracted once with 200 ml
  4. customThe aqueous layer was separated
  5. temperaturecooling
  6. filtrationThe precipitate was filtered
  7. customrecrystallized once with acetonitrile
  8. customThin-layer chromatography gave a single spot

Sources & evidence

ORD record
ord-d60f80e944af43b08d121e01b0425d39
Source dataset
uspto-grants-1977_08
Patent number
US04044021

Reaction notes

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