Triethylamine → HCID 23144527, compound

HRID 337525Notes

Reaction equation

HRID 337525 reaction equation
Br.Br[CH:3]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[C:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=O.C(N(CC)CC)C.[NH2:24][C:25]([NH2:27])=[S:26].C(=O)([O-])O.[Na+]>C(O)C>[NH2:27][C:25]1[S:26][C:3]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:4]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[N:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 23144418HCID 23144418, compound

Product 1

HCID 23144527HCID 23144527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1-(2-furyl)-2-(4-pyridyl)ethanone hydrobromide (7.59 g, 21.9 mmol) was suspended in ethanol (110 mL), and triethylamine (3.35 mL, 24.1 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. Thiourea (1.83 g, 24.1 mmol) was added to the reaction mixture, followed by stirring under heating and reflux for 30 minutes. The reaction mixture was allowed to cool down to room temperature, and then a saturated aqueous solution of sodium hydrogencarbonate was added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=10:1) to afford the entitled Compound a (5.10 g, 96%) as pale yellow crystals.

Workup

  1. stirringby stirring
  2. temperatureunder heating
  3. temperaturereflux for 30 minutes
  4. temperatureto cool down to room temperature
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=10:1)
  10. customto afford the entitled Compound a (5.10 g, 96%) as pale yellow crystals

Sources & evidence

ORD record
ord-d2ede73eb678457e9aaed26f64c96f2a
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

Loading…