Potassium Carbonate → HCID 19612626, compound

HRID 1600313Notes

Reaction equation

HRID 1600313 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 1h. 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

Sources & evidence

ORD record
ord-a0897d5b8b2347eab961c7282131685f
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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