1-Hexanethiol → HCID 22413525, compound

HRID 1721614Notes

Reaction equation

HRID 1721614 reaction equation
[CH2:1]([SH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[Cl:10][C:11]1[C:16](Cl)=[N:15][CH:14]=[CH:13][N:12]=1>C1COCC1>[Cl:10][C:11]1[C:16]([S:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:15][CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 24758Sodium hydrideHCID 785752,3-Dichloropyrazine

Product 1

HCID 22413525HCID 22413525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

Hexanethiol (4.7 g, 40 mmole) was added to a slurry of sodium hydride (0.96 g) in THF (60 ml), and the mixture stirred for 30 minutes. The slurry was cooled to -5° C. and a solution of 2,3-dichloropyrazine (6 g) added. The mixture was stirred for 1.5 hours, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel using varying concentrations of methanol in chloroform. Fractions containing the desired product were evaporated, yielding 2-chloro-3-hexylsulfanyl pyrazine. as an oil.

Workup

  1. stirringThe mixture was stirred for 1.5 hours
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customThe residue was purified by column chromatography on silica gel using
  5. additionFractions containing the desired product
  6. customwere evaporated

Sources & evidence

ORD record
ord-1043458148a145cf9edb4c31b7bb4af8
Source dataset
uspto-grants-1996_04
Patent number
US05512574

Reaction notes

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