Chlorosuccinimide → 3,7-Dichloro-5-ethylpyrazolo[1,5-a]pyrimidine

HRID 1450371Notes

Reaction equation

HRID 1450371 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=1.[Cl:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:13][C:10]1[CH:9]=[N:8][N:7]2[C:2]([Cl:1])=[CH:3][C:4]([CH2:11][CH3:12])=[N:5][C:6]=12

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 105354107-Chloro-5-ethylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 106324843,7-Dichloro-5-ethylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.5 g (30 mmol) of the chloro compound (Example 1, Step B) and 4.0 g (30 mmol) of N-chlorosuccinimide were dissolved in 150 ml chloroform, stirred for 4 h at room temperature, and finally heated for some minutes on a steam bath. The mixture was poured on to ice water, the aqueous layer extracted with dichloromethane, the combined organic layers washed twice with saturated sodium carbonate solution, dried over sodium sulfate, and evaporated in in vacuo. The title compound was obtained as an oil after chromatography on silica gel with dichloromethane.

Workup

  1. temperaturefinally heated for some minutes on a steam bath
  2. extractionthe aqueous layer extracted with dichloromethane
  3. washthe combined organic layers washed twice with saturated sodium carbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated in in vacuo

Sources & evidence

ORD record
ord-7bb056b913c64aea94f5a54215db64f2
Source dataset
uspto-grants-1997_02
Patent number
US05602137

Reaction notes

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