Sodium Bicarbonate → HCID 90044011, compound

HRID 1478551Notes

Reaction equation

HRID 1478551 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12](=[S:14])[NH2:13])[CH:9]=[N:8]2)[CH:2]=1.Br[C:16]1[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[C:17]=1O.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[S:14][C:16]4[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[C:17]=4[N:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 64250832-Cyclohexen-1-one, 3-bromo-2-hydroxy-HCID 90043700HCID 90043700, compound

Product 1

HCID 90044011HCID 90044011, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-(3-pyridyl)pyrazole-4-carbothioamide (2.50 mmol, 0.510 g) and 3-bromo-2-hydroxy-cyclohex-2-en-1-one (2.50 mmol, 0.477 g, described in Tet. Lett. 2011, 52, 3633) were suspended in 10 ml acetic acid and the reaction mixture heated to reflux for 20 h. The reaction was cooled down to room temperature, diluted with water, slowly neutralised by dropwise addition in a saturated NaHCO3 solution, and the aqueous phase was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated. The crude material was purified by Combiflash to give a solid which was crystallized in diethylether to yield the title compound as a light yellow solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 20 h
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by Combiflash
  8. customto give a solid which
  9. customwas crystallized in diethylether

Sources & evidence

ORD record
ord-c0b0ad6161f044fbab30f3da3b5d0831
Source dataset
uspto-grants-2016_08
Patent number
US09403845B2

Reaction notes

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