Sodium hydride → HCID 894754, compound

HRID 2247796Notes

Reaction equation

HRID 2247796 reaction equation
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:5])[CH3:4].[H][H].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1>O.CN(C)C=O>[F:24][C:23]([F:26])([F:25])[C:20]1[CH:21]=[CH:22][C:17]([O:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH:3]([CH3:5])[CH3:4])=[CH:8][CH:9]=2)=[N:18][CH:19]=1

Participants

7

Reactant 4

HCID 24758Sodium hydride2×HCID 820014-IsopropoxyphenolHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 894754HCID 894754, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.7 g, 0.154 mole) was added in portions to a stirred mixture of dry N,N-dimethylformamide (60 ml) and 4-isopropyloxyphenol (26 g, 0.17 mole). After hydrogen evolution had stopped, 2-chloro-5-trifluoromethylpyridine (28.75 g, 0.158 mole) was added and stirring was continued for 1.75 hours at 80°-95° C. Further sodium hydride (0.4 g) was added. After stirring for 1.25 hours at 95° C., the mixture was cooled and poured into water. The water was extracted twice with toluene, the extracts washed with 1M sodium hydrogen carbonate and brine, filtered and evaporated to a brown oily residue which was purified over silica gel with 1:9 ether/hexane as eluant to give the title compound (37.34 g).

Workup

  1. stirringAfter stirring for 1.25 hours at 95° C.
  2. temperaturethe mixture was cooled
  3. extractionThe water was extracted twice with toluene
  4. washthe extracts washed with 1M sodium hydrogen carbonate and brine
  5. filtrationfiltered
  6. customevaporated to a brown oily residue which
  7. customwas purified over silica gel with 1:9 ether/hexane as eluant

Sources & evidence

ORD record
ord-c4fb5fd7ce434027bb37939b0c299416
Source dataset
uspto-grants-1991_08
Patent number
US05037759

Reaction notes

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