Potassium Carbonate → HCID 19612626, compound

HRID 1728645Notes

Reaction equation

HRID 1728645 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-e6acf5da357b409bb484471ce0322c49
Source dataset
uspto-grants-1994_07
Patent number
US05328924

Reaction notes

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