Diethyl Ether → HCID 2809345, compound

HRID 2377690Notes

Reaction equation

HRID 2377690 reaction equation
Cl[C:2]1[C:3]([CH:12]=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[SH:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(OCC)C>CN(C)C=O.ClCCl>[F:11][C:8]([F:9])([F:10])[C:6]1[CH:7]=[C:2]2[S:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][C:3]2=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 220187903-Chloro-5-(trifluoromethyl)picolinaldehyde

Product 1

HCID 2809345HCID 2809345, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-Chloro-5-(trifluoromethyl)-2-pyridinecarbaldehyde (Chemical Abstracts number 175277-50-6, purchase from Maybridge), potassium carbonate (4.95 g), and ethyl mercaptoacetate (2.52 g) were combined in N,N-dimethylformamide (25 mL) at 25° C. and stirred for 18 hours. The mixture was then heated at 50° C. for 6 hours, allowed to cool to room temperature, poured into a mixture of diethyl ether (80 mL) and dichloromethane (25 mL), and washed with aqueous sodium carbonate. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was dissolved in dichloromethane and filtered to remove solids. The filtrate was concentrated and the residue purified by flash chromatography (dichloromethane) to provide the title compound. MS (DCI/NH3) m/z 276.0 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with aqueous sodium carbonate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. filtrationfiltered
  8. customto remove solids
  9. concentrationThe filtrate was concentrated
  10. customthe residue purified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-9a8f803ef61b491c9eaa9b5d542a0211
Source dataset
uspto-grants-2008_12
Patent number
US07470691B2

Reaction notes

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