Chlorosuccinimide → HCID 22036518, compound

HRID 493339Notes

Reaction equation

HRID 493339 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 (11 M 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. (C8H10Cl2N4.⅓H2O) 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-19f62aaf4e994ed2b1c45060de9c0c3c
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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