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

HRID 2163957Notes

Reaction equation

HRID 2163957 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. Extracton with isopropyl alcohol, with the removal of some polymeric material and the addition of ether gave a cream coloured solid (3.5 g.), which was recrystallised from ethanol-ether to furnish 2-[(2aminoethyl)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. customExtracton with isopropyl alcohol, with the removal of some polymeric material
  10. additionthe addition of ether
  11. customgave a cream coloured solid (3.5 g.), which
  12. customwas recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-2e4b32cd300b4e0b96360eaf574da4f7
Source dataset
uspto-grants-1979_01
Patent number
US04137237

Reaction notes

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