Hydrochloric Acid → 3-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-6-methylpyridine

HRID 965122Notes

Reaction equation

HRID 965122 reaction equation
O.[SH2:2].[Na].Cl[C:5]1[C:9]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:8][S:7][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>CN(C=O)C>[CH2:23]([S:2][C:5]1[C:9]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:8][S:7][N:6]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 190752683-(3-Chloro-1,2,5-thiadiazol-4-yl)-6-methylpyridineHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 190753693-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydrogen sulfide monohydrate (0.33 g, 4.4 mmol) was added to a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-6-methylpyridine (0.85 g, 4 mmol) in DMF (20 ml) at room temperature and the reaction mixture was stirred for 1 h. Potassium carbonate (1.65 g, 12 mmol) and 1-hexylbromide (0.99 g, 6 mmol) were added and the reaction mixture was stirred for additionally 24 h. 1N HCl was added and the reaction mixture was extracted once with ether. The aqueous phase was basified with 50% NaOH and extracted with ether. The ether phases were dried and evaporated to give crude title compound.

Workup

  1. stirringthe reaction mixture was stirred for additionally 24 h
  2. extractionthe reaction mixture was extracted once with ether
  3. extractionextracted with ether
  4. dry with materialThe ether phases were dried
  5. customevaporated

Sources & evidence

ORD record
ord-752882fe15e84a0c92bc2f7cc242f1fa
Source dataset
uspto-grants-1998_06
Patent number
US05773452

Reaction notes

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