Hydrochloric Acid → 2-[(2-Aminoethyl)thiomethyl]pyrazine hydrochloride

HRID 26843

Reaction equation

HRID 26843 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.[Na].Cl.[NH2:11][CH2:12][CH2:13][SH:14].Cl>C(O)C>[ClH:1].[NH2:11][CH2:12][CH2:13][S:14][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9082Cysteamine HydrochlorideHCID 170169Pyrazine, 2-(chloromethyl)-HCID 5360545Sodium

Product 1

HCID 205578042-[(2-Aminoethyl)thiomethyl]pyrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethylpyrazine (6.4 g.) was added over 20 minutes to a solution freshly prepared from sodium (0.23 g.) in ethanol (50 ml.) to which cysteamine hydrochloride (5.7 g.) had been added gradually at 0° and stirred at this temperature for 2 hours. The suspension finally obtained was stirred at room temperature overnight, acidified with hydrochloric acid (pH 5) and concentrated under reduced pressure. The dry residue was extracted with ethanol and the extracts filtered and concentrated to give the crude product. Extraction with isopropyl alcohol, with the removal of some polymeric material and the addition of ether gave a cream colored solid (3.5 g.), which was recrystallised from ethanol-ether to furnish 2-[(2-aminoethyl)thiomethyl]pyrazine hydrochloride, m.p. 144°-146°.

Workup

  1. additionhad been added gradually at 0°
  2. customThe suspension finally obtained
  3. stirringwas stirred at room temperature overnight
  4. concentrationconcentrated under reduced pressure
  5. extractionThe dry residue was extracted with ethanol
  6. filtrationthe extracts filtered
  7. concentrationconcentrated
  8. customto give the crude product
  9. extractionExtraction with isopropyl alcohol
  10. customwith the removal of some polymeric material
  11. additionthe addition of ether
  12. customgave a cream colored solid (3.5 g.), which
  13. customwas recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-0f8783500cad4e078754c0b9ea69f252
Source dataset
uspto-grants-1979_04
Patent number
US04151288

Linked notes

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