Methanethiol → 2-Chloro-6-(methylsulfanyl)pyrazine

HRID 1679661Notes

Reaction equation

HRID 1679661 reaction equation
[Na].[H-].[Na+].[CH3:4][SH:5].[Cl:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9](Cl)[N:8]=1>C1C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([S:5][CH3:4])[N:8]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 5360545Sodium

Product 1

HCID 203616852-Chloro-6-(methylsulfanyl)pyrazine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.13 mole of sodium methylmercaptide (prepared from 3.12 g. sodium hydride and excess methyl mercaptan), 20 g. (0.13 mole) of 2,6-dichloropyrazine and 200 ml. benzene is heated at reflux for 24 hours, cooled and washed twice with 50 ml. water. The benzene layer is separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Distillation of the residue gives 2-chloro-6-methylthiopyrazine.

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturecooled
  3. washwashed twice with 50 ml
  4. customThe benzene layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-51ce95e9ccca438d8bee797a9daa1d48
Source dataset
uspto-grants-1978_03
Patent number
US04081542

Reaction notes

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