Hydrochloric Acid → HCID 20318381, compound

HRID 866752Notes

Reaction equation

HRID 866752 reaction equation
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].Cl[C:14]1[CH:15]=[N+:16]([O-:20])[CH:17]=[CH:18][N:19]=1.Cl[CH2:22][S:23][C:24]#[N:25].Cl>CN(C)C=O>[S:23]([CH2:22][S:10][C:14]1[CH:15]=[N+:16]([O-:20])[CH:17]=[CH:18][N:19]=1)[C:24]#[N:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 76755Thiocyanic acid, chloromethyl esterHCID 3429253-Chloropyrazine 1-oxide

Product 1

HCID 20318381HCID 20318381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a vigorously stirred solution of 9.6 grams (0.04 mole) of sodium sulfide nonahydrate in 100 milliliters of dimethylformamide was gradually added 5.2 grams (0.04 mole) of 3-chloropyrazine-1-oxide in 50 milliliters of dimethylformamide. The reaction mixture was stirred overnight at 45°-50° C. Thereafter, 4.3 grams (0.04 mole) of chloromethylthiocyanate were gradually added and the mixture stirred for 4 hours. At the completion of the reaction, the dimethylformamide was removed by evaporation under reduced pressure and the residue was dissolved in a mixture of water and chloroform. Two phases formed and the aqueous phase was acidified with hydrochloric acid and extracted with chloroform. The organic portions were combined and washed with both a saturated sodium bicarbonate solution and a saturated sodium chloride solution and dried over magnesium sulfate. The chloroform was thereafter removed by evaporation leaving the 3-(thiocyanatomethylthio)pyrazine-1-oxide as a residue. The product was recrystallized from methanol and was recovered in a yield of 4.75 grams (60 percent of theoretical). The product melted at 104°-106° C and upon analysis was found to have carbon, hydrogen, nitrogen and sulfur contents of 36.40, 2.66, 20.59 and 32.20 percent, respectively, as compared with the theoretical contents of 36.18, 2.51, 21.11 and 32.16 percent, respectively, as calculated for the above-named compound.

Workup

  1. stirringthe mixture stirred for 4 hours
  2. customAt the completion of the reaction
  3. customthe dimethylformamide was removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in a mixture of water and chloroform
  5. customTwo phases formed
  6. extractionextracted with chloroform
  7. washwashed with both a saturated sodium bicarbonate solution
  8. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  9. customThe chloroform was thereafter removed by evaporation

Sources & evidence

ORD record
ord-85ddacec3da5437598a6425aa0936be0
Source dataset
uspto-grants-1978_07
Patent number
US04101546

Reaction notes

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