Chlorosuccinimide → HCID 22036518, compound

HRID 991682Notes

Reaction equation

HRID 991682 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:5]=[C:4]([Cl:14])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 140864382-Chloro-3-(piperazin-1-yl)pyrazine

Product 1

HCID 22036518HCID 22036518, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-chloro-3-(1-piperazinyl)pyrazine (11.7 g, 58.7 mmol; from Example 90, Step 1) in CHCl3 (50 mL) was N-chlorosuccinimid (14.4 g, 108 mmol) added and the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature and extracted twice with water. The combined aqueous phases were made alkaline (11M NaOH), saturated with NaCl, cooled, and extracted with EtOAc (×3). Concentration of the combined, dried (MgSO4), organic phases afforded 6.12 g (45%) of the title compound as a brown oil which crystallized upon standing: mp 89-97° C. Anal. (C8H10Cl2N4.1/3H2O) C, H, N.

Workup

  1. additionadded
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 30 minutes
  4. extractionextracted twice with water
  5. temperaturesaturated with NaCl, cooled
  6. extractionextracted with EtOAc (×3)
  7. dry with materialdried (MgSO4), organic phases

Sources & evidence

ORD record
ord-269becb54adf434d9ac80cbaeb04d63b
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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