Triethylamine → HCID 22618004, compound

HRID 725816Notes

Reaction equation

HRID 725816 reaction equation
P(Cl)(Cl)([Cl:3])=O.C(N(CC)CC)C.[CH2:13]([C:17]1[CH:22]=[C:21](O)[N:20]2[N:24]=[CH:25][CH:26]=[C:19]2[N:18]=1)[CH2:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1>[CH2:13]([C:17]1[CH:22]=[C:21]([Cl:3])[N:20]2[N:24]=[CH:25][CH:26]=[C:19]2[N:18]=1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178441198HCID 178441198, compound

Product 1

HCID 22618004HCID 22618004, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus oxychloride (80 ml) and triethylamine (44 ml) were added to a toluene suspension (400 ml) containing 40 g of the crystals obtained in step (1). The reaction mixture was refluxed with heating for 4 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was poured into ice water. The mixture was neutralized with sodium acetate and extracted with ethyl acetate. The organic layer was collected, washed with a saturated saline solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:9) to provide 41 g of 5-n-butyl-7-chloropyrazolo[1,5-a]pyrimidine as a light yellow oily compound.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperaturewith heating for 4 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionthe residue was poured into ice water
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was collected
  8. washwashed with a saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:9)

Sources & evidence

ORD record
ord-14814b8e6b1a4374b03f69ad74b6ac46
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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