Chlorosuccinimide → 3,7-Dichloro-6-(2-chloroethyl)-5-methylpyrazolo[1,5-a]-pyrimidin

HRID 345092Notes

Reaction equation

HRID 345092 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[N:15]2[N:16]=[CH:17][CH:18]=[C:14]2[N:13]=[C:12]([CH3:19])[C:11]=1[CH2:20][CH2:21][Cl:22]>C(Cl)(Cl)Cl>[Cl:1][C:18]1[CH:17]=[N:16][N:15]2[C:10]([Cl:9])=[C:11]([CH2:20][CH2:21][Cl:22])[C:12]([CH3:19])=[N:13][C:14]=12

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 156758537-Chloro-6-(2-chloroethyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 156758563,7-Dichloro-6-(2-chloroethyl)-5-methylpyrazolo[1,5-a]-pyrimidinYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.60 g (12 mmoles) of N-chlorosuccinimide were added to a solution of 2.30 g (10 mmoles) of 7-chloro-6-(2-chloroethyl)-5-methylpyrazolo[1.5-a]pyrimidine (prepared as described in Example 3) in 10 ml of chloroform, and the resulting mixture was heated under reflux, with stirring, for one hour. At the end of this time, the reaction mixture was washed with a 2N aqueous solution of potassium hydroxide and then with water, after, which it was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through alumina (eluted with chloroform) and recrystallized from diisopropyl ether to afford 1.56 g (yield 59%) of the title compound as light yellow needles, melting at 115°-117° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. washAt the end of this time, the reaction mixture was washed with a 2N aqueous solution of potassium hydroxide
  4. dry with materialwith water, after, which it was dried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through alumina (eluted with chloroform)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5ce42f6028954e6f94b8ee30c5b73641
Source dataset
uspto-grants-1991_10
Patent number
US05055479

Reaction notes

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