Potassium Carbonate → HCID 19612626, compound

HRID 1734558Notes

Reaction equation

HRID 1734558 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-44988a2ca2fb48adab2c0ac1c7493865
Source dataset
uspto-grants-1996_07
Patent number
US05534528

Reaction notes

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