Water → HCID 22024377, compound

HRID 500985Notes

Reaction equation

HRID 500985 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][N:14]=1.[Cl:16]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Cl:16][C:13]1[N:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:10]([NH2:15])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 22024361HCID 22024361, compound

Product 1

HCID 22024377HCID 22024377, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(2,4-Dichlorophenyl)-2-pyrazinamine (1.43 g, 6.0 mmol) was dissolved in chloroform (9 mL), N-chlorosuccinimide (0.96 g, 7.2 mmol) was added thereto, and the mixture was stirred by heating under reflux for 4 hours. After being allowed to cool, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2) to give the title compound (1.54 g) as yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-dcee610bde9543cd83e55cee5823a5ad
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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