Sulfuric Acid → HCID 12857636, compound

HRID 1395542Notes

Reaction equation

HRID 1395542 reaction equation
[CH:1]([N:4]([CH:18]([CH3:20])[CH3:19])[CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11](C#N)=[C:10]([Cl:17])[N:9]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>[CH:18]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([Cl:17])[N:9]=1)([CH3:19])[CH3:20]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 12857634HCID 12857634, compound

Product 1

HCID 12857636HCID 12857636, compound

Procedure

A solution of crude 2-(2-diisopropylaminoethylamino)-4-methyl-5-cyano-6-chloropyridine (4.0 g) in 20 ml of 50% (by volume) sulfuric acid is stirred at reflux for 16 hours over night. The solution is cooled and is cautiously poured into excess saturated sodium carbonate. The basic mixture is extracted with methylene chloride. After washing the extract with water, drying and filtering through activated carbon, the solvent is removed in vacuo. This gives 3.1 g of pale yellow oil which slowly solidifies. Extraction of the crude solid with hexane, cooling in dry ice-acetone and filtering gives 1.9 g. of white solid. The purified product melts at 64°-66° C.

Workup

  1. temperatureat reflux for 16 hours over night
  2. temperatureThe solution is cooled
  3. extractionThe basic mixture is extracted with methylene chloride
  4. washAfter washing the
  5. extractionextract with water
  6. customdrying
  7. filtrationfiltering through activated carbon
  8. customthe solvent is removed in vacuo
  9. extractionExtraction of the crude solid with hexane
  10. temperaturecooling in dry ice-acetone
  11. filtrationfiltering
  12. customgives 1.9 g

Sources & evidence

ORD record
ord-a9ce7fdb7ff84b7fab0402056bfe919a
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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