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

HRID 1600320Notes

Reaction equation

HRID 1600320 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.[OH-].[Na+]>CN(C=O)C.CCOCC>[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

9

Reactant 6

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 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 2

HCID 3283Diethyl EtherSolvent2×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, 4mmol) 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 extractedonce with ether. The aqueous phase was basified with 50% NaOH and extractedwith 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. dry with materialThe ether phases were dried
  3. customevaporated

Sources & evidence

ORD record
ord-f91d45befd534952afd9cdcebe73ca03
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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