Hydrochloric Acid → HCID 86595533, compound

HRID 644414Notes

Reaction equation

HRID 644414 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 (Compound No. 52; 4.75 g, 10 mmol), chloromethyl methyl ether (1.14 ml, 15 mmol), 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 (n-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 (n-hexane:ethyl acetate=3:1)
  7. customrecrystallized (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bac4eb69d22e40dbbcc84e88346681a7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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