Hydrochloric Acid → HCID 86595533, compound

HRID 2384369Notes

Reaction equation

HRID 2384369 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:26][O:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:16]=2[O:22][CH2:26][O:27][CH3:28])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 11190699N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodo-benzamide

Product 1

HCID 86595533HCID 86595533, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodobenzamide (4.75 g, 10 mmol), chloromethyl methyl ether (1.14 ml, 15 ml), potassium carbonate (2.76 g, 20 mmol) and acetone (50 mL) was refluxed for 8 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=3:1), and recrystallized (n-hexane/ethyl acetate) to give the title compound (3.96 g, 76.3%) as a white solid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified by chromatography on silica gel (hexane:ethyl acetate=3:1)
  7. customrecrystallized (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bf638491319a4adabbe6b504fd20fe5d
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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