Sodium Sulfide → HCID 20263918, compound

HRID 972862Notes

Reaction equation

HRID 972862 reaction equation
CO[CH:3]([O:12]C)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][N:5]=1.[S-2:14].[Na+].[Na+]>O>[CH:3]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:14][S:14][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:12])=[N:5][CH:6]=2)=[CH:6][N:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 20263920HCID 20263920, compound

Product 1

HCID 20263918HCID 20263918, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.1 mole of 2-di(methoxy)methyl-5-chloromethylpyridine in absolute alcohol (150 ml.) is added dropwise at 10°-15° C. over 20 minutes, to a suspension of 6 g. of sodium sulfide (Na2S2) in 50 ml. of absolute alcohol. The mixture stirred at room temperature for 1/2 hour, then 15 min. at 40°-50° C. and poured into 800 ml. of water. The mixture is extracted with ether and the extract is dried over magnesium sulfate and concentrated to an oil. The oil is dissolved in 80 ml. of 1 N hydrochloric acid and heated for 2- min. at 40° C. The mixture is cooled, adjusted to pH 7 with sodium bicarbonate and extracted with ethylacetate. The extract is dried over magnesium sulfate and concentrated to dryness to give bis[2-formyl-5-pyridylmethyl]disulfide.

Workup

  1. addition15 min. at 40°-50° C. and poured into 800 ml
  2. extractionThe mixture is extracted with ether
  3. dry with materialthe extract is dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. dissolutionThe oil is dissolved in 80 ml
  6. temperatureof 1 N hydrochloric acid and heated for 2- min
  7. customat 40° C
  8. temperatureThe mixture is cooled
  9. extractionextracted with ethylacetate
  10. dry with materialThe extract is dried over magnesium sulfate
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-602a9749551e4a5da97c0bc533394f65
Source dataset
uspto-grants-1977_10
Patent number
US04053606

Reaction notes

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