Thionyl Chloride → HCID 68527082, compound

HRID 884146Notes

Reaction equation

HRID 884146 reaction equation
O[CH2:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:31])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:31][CH2:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68525933HCID 68525933, compound

Product 1

HCID 68527082HCID 68527082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-(4-hydroxymethylphenoxy)pyridin-3-yl]-4-trifluoromethylbenzamide (3.06 g, 7.9 mmol) in dichloromethane (90 mL) was added thionyl chloride (1.7 mL, 23.3 mmol), and the resulting solution was stirred for 4 hours at room temperature. To the residue was added a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was washed with diethyl ether, to thereby yield 2.95 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-ceae0d6b3b1e45fb960061626cf1b6ba
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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