Hydrochloric Acid → 2-[(2-Methylfuran-3-yl)sulfanyl]-3-(2-methylpropyl)pyrazine

HRID 1288616Notes

Reaction equation

HRID 1288616 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[SH:10].Cl[C:12]1[C:17]([CH2:18][CH:19]([CH3:21])[CH3:20])=[N:16][CH:15]=[CH:14][N:13]=1.Cl>CO.CCCCCC.O>[CH2:18]([C:17]1[C:12]([S:10][C:9]2[CH:8]=[CH:7][O:6][C:5]=2[CH3:4])=[N:13][CH:14]=[CH:15][N:16]=1)[CH:19]([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 342862-Methyl-3-furanthiolHCID 5218142-Chloro-3-isobutylpyrazineHCID 10942334Sodium Methoxide2×

Product 1

HCID 215030922-[(2-Methylfuran-3-yl)sulfanyl]-3-(2-methylpropyl)pyrazine

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
65 °C

Procedure

Into a 25 ml round bottom 3 neck flask equipped with magnetic stirrer, Y tube, nitrogen inlet, and reflux condenser with calcium chloride drying tube is placed a solution of 0.15 g (0.0028 moles) of sodium methoxide in 2 ml absolute methyl alcohol. To the sodium methoxide solution, while maintaining the temperature at 22° - 25° C, is added 0.32 g (0.0028 moles) of 2-methyl-3-furan thiol dissolved in 2 ml absolute methanol. The reaction mass is stirred for a period of 10 minutes at 22° - 25° C at which time a solution of 0.43 g (0.0025 moles) of 2-chloro-3-isobutyl-pyrazine in 2 ml absolute methanol is added dropwise over a period of 2 minutes. The reaction mass is then heated to reflux at 65° C under nitrogen and maintained at reflux for a period of 4 hours. At the end of the 4 hour reflux period, the reaction mass is cooled to room temperature. 10 ml of water is added to the reaction mass which is then neutralized to a pH of 5 with dilute hydrochloric acid. Two 7 ml portions of n-hexane are then used to extract the reaction mass. The hexane layers are separated, combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to a red amber oil weighing 0.51 g. The major material is isolated using GLC techniques (conditions: 8 feet × 1/4inche SE-30 column) and is confirmed by NMR, IR and Mass Spectral Analysis to be a material having the structure: ##SPC15##

Workup

  1. customInto a 25 ml round bottom 3 neck flask equipped with magnetic stirrer
  2. temperatureY tube, nitrogen inlet, and reflux condenser with calcium chloride drying tube
  3. additionis added dropwise over a period of 2 minutes
  4. temperatureThe reaction mass is then heated
  5. temperaturemaintained
  6. temperatureat reflux for a period of 4 hours
  7. temperatureAt the end of the 4 hour reflux period
  8. temperaturethe reaction mass is cooled to room temperature
  9. extractionto extract the reaction mass
  10. customThe hexane layers are separated
  11. washwashed with saturated sodium chloride solution
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated to a red amber oil
  14. customThe major material is isolated

Sources & evidence

ORD record
ord-8519dd5334d54d7e89cfce98738f836b
Source dataset
uspto-grants-1976_10
Patent number
US03988510

Reaction notes

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