HCID 71152016, compound → HCID 71152102, compound

HRID 2174186Notes

Reaction equation

HRID 2174186 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[CH:7]([OH:9])[CH3:8].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[C:7](=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 71152016HCID 71152016, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 71152102HCID 71152102, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-[4-chloro-2-(3-pyridyl)thiazol-5-yl]ethanol (120 mg, 0.5 mmol) was dissolved in 1,2-dichloroethane (10 ml). Pyridinium chlorochromate (216 mg, 1 mmol) was added to the reaction mixture. The reaction mixture was stirred at 70° C. for 3 hours, cooled to ambient temperature, poured onto a silica gel plug and eluted with dichloromethane. The eluent was evaporated under reduced pressure, and the residue dried to dryness to get 1-[4-chloro-2-(3-pyridyl)thiazol-5-yl]ethanone in form of a white solid. 1H NMR (300 Mz, DMSO-d6): δ: 9.17 (s, 1H), 8.75 (d, 1H, J=4.8 Hz), 8.37 (d, 1H, J=8.1 Hz), 7.58 (m, 1H), 2.66 (s, 3H).

Workup

  1. temperaturecooled to ambient temperature
  2. additionpoured onto a silica gel plug
  3. washeluted with dichloromethane
  4. customThe eluent was evaporated under reduced pressure
  5. customthe residue dried to dryness

Sources & evidence

ORD record
ord-812f1888207b417f8c5b320b8d63089d
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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