Potassium Carbonate → HCID 19612626, compound

HRID 1291533Notes

Reaction equation

HRID 1291533 reaction equation
O.[SH2:2].[Na].Cl[C:5]1[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:8][O:7][N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.O>[C:26]1([CH2:25][CH2:24][CH2:23][S:2][C:5]2[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:8][O:7][N:6]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 15180172HCID 15180172, compoundHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 19612626HCID 19612626, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydrogen sulfide monohydrate (0.74 g, 10.5 mmol) was added to a solution of 3-(3-chloro-1,2,5-oxadiazol-4-yl)pyridine (1.27, 7.0 mmol) in DMF (30 ml) at room temperature and the reaction mixture was stirred for 1 h. Potassium carbonate (2.0 g, 14.5 mmol) and 1-bromo-3-phenylpropane (2.4 g, 12 mmol) were added and the reaction mixture was stirred for additionally 24 h. Water (50 ml) was added and extracted with ether. The combined ether phases were dried and evaporated. Purification by column chromatography (SiO2, eluent: ethyl acetate/methylene chloride (1:1)) gave the title compound.

Workup

  1. stirringthe reaction mixture was stirred for additionally 24 h
  2. extractionextracted with ether
  3. dry with materialThe combined ether phases were dried
  4. customevaporated
  5. customPurification by column chromatography (SiO2, eluent: ethyl acetate/methylene chloride (1:1))

Sources & evidence

ORD record
ord-830f9b96c4e14d9aa06032aafd95f4bb
Source dataset
uspto-grants-1998_05
Patent number
US05753683

Reaction notes

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