5-Pyrazin-2-yldithiole-3-thione → HCID 136409745, compound

HRID 1439252Notes

Reaction equation

HRID 1439252 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[S:11][S:10][C:9](=S)[CH:8]=1.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO.O>[OH:15][N:14]=[C:9]1[CH:8]=[C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[S:11][S:10]1

Participants

6

Reactant 3

HCID 1823325-Pyrazin-2-yldithiole-3-thioneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 136409745HCID 136409745, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 5-(pyrazin-2-yl)-1,2-dithiole-3-thione (31.85 g.) in methanol (1,400 cc.) is heated at a temperature of about 65° C. Hydroxylamine hydrochloride (24 g.), followed by sodium acetate (35 g.) dissolved in water (75 cc.), are then added. The reaction mixture is then heated for 3 hours at a temperature of about 65° C. After cooling to a temperature of about 20° C., the insoluble product is filtered off and is then washed with methanol (4 × 100 cc.) and with carbon disulphide (4 × 100 cc.). The product is dissolved in dimethylformamide (300 cc.) at 100° C. and is then reprecipitated by adding water (600 cc.). After filtration and drying, 3-hydroxyimino-5-(pyrazin-2-yl)-1,2-dithiole (23 g.) melting at 262° C. is obtained.

Workup

  1. additionare then added
  2. temperatureThe reaction mixture is then heated for 3 hours at a temperature of about 65° C
  3. temperatureAfter cooling to a temperature of about 20° C.
  4. filtrationthe insoluble product is filtered off
  5. washis then washed with methanol (4 × 100 cc.) and with carbon disulphide (4 × 100 cc.)
  6. dissolutionThe product is dissolved in dimethylformamide (300 cc.) at 100° C.
  7. customis then reprecipitated
  8. additionby adding water (600 cc.)
  9. filtrationAfter filtration
  10. customdrying

Sources & evidence

ORD record
ord-1853223adb6a4dceaa077131b4ddf4d0
Source dataset
uspto-grants-1977_11
Patent number
US04058611

Reaction notes

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