HCID 22247839, compound → HCID 85860271, compound

HRID 889851Notes

Reaction equation

HRID 889851 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[N:6]1.[C:16]([O-:19])(=[S:18])[CH3:17].[K+]>CC(C)=O>[C:16](=[O:19])([S:18][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[N:6]1)[CH3:17]

Participants

4

Reactant 2

HCID 22247839HCID 22247839, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 85860271HCID 85860271, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.23 g (1.04 mmol) 1-(3-chloroprop-1-yl)-4-phenyl-1H-pyrazole were dissolved in 6 ml acetone, potassium thioacetate (0.15 g, 1.3 mmol) was added and the mixture was heated to reflux during 16 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (hexane/ethyl acetate, gradient 9:1 to 7:3) to give 240 mg of the desired product as a yellow oil. MS (EI): 260.1 (M+). 1H-NMR (CDCl3): 2.19 (quint, 2H), 2.35 (s, 3H), 2.87 (t, 2H), 4.21 (t, 2H), 7.23 (m, 1H), 7.36 (m, 1H), 7.47 (m, 1H), 7.64 (s, 1H), 7.78 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux during 16 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate, gradient 9:1 to 7:3)

Sources & evidence

ORD record
ord-c79ef1c6faba496cb72395035c8e9e26
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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