Isopropylamine → 3-Chloro-N-(propan-2-yl)pyrazin-2-amine

HRID 1449708Notes

Reaction equation

HRID 1449708 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH:9]([NH2:12])([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]([NH:12][CH:9]([CH3:11])[CH3:10])=[N:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 785752,3-Dichloropyrazine

Product 1

HCID 214776373-Chloro-N-(propan-2-yl)pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,3-dichloropyrazine (2.0 g) and isopropylamine (2.3 g) in toluene (8 ml) is refluxed for 40 hr. The mixture is cooled and filtered to remove isopropylamine hydrochloride. The filtrate is concentrated in vacuo to a residue which is diluted with an aqueous sodium hydroxide solution (10%) and dichloromethane. The phases are separated. The dichloromethane phase is washed with saline, dried over sodium sulfate, and concentrated to give the title compound, NMR (CDCl3) 1.28, 4.21, 5.02, 7.54 and 7.94 δ.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. customto remove isopropylamine hydrochloride
  4. concentrationThe filtrate is concentrated in vacuo to a residue which
  5. additionis diluted with an aqueous sodium hydroxide solution (10%) and dichloromethane
  6. customThe phases are separated
  7. washThe dichloromethane phase is washed with saline
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-71370d5db69d4a06bc1027d8bd77c1af
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

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