Hydrochloric Acid → HCID 11475621, compound

HRID 644420Notes

Reaction equation

HRID 644420 reaction equation
[C:1]([C:6]1[CH:7]=[CH:8][C:9]([O:29]C)=[C:10]([CH:28]=1)[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:12])(=[O:5])[CH:2]([CH3:4])[CH3:3].N1C(C)=CC(C)=CC=1C.[I-].[Li+].Cl>>[F:21][C:20]([F:22])([F:23])[C:18]1[CH:19]=[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:28]=[C:6]([C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[CH:7]=[CH:8][C:9]=2[OH:29])[CH:15]=[C:16]([C:24]([F:26])([F:27])[F:25])[CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 23069968HCID 23069968, compound

Product 1

HCID 11475621HCID 11475621, compoundYield 65.3%

Procedure

A mixture of 5-isobutyryl-N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxybenzamide (143.4 mg, 0.33 mmol), 2,4,6-collidine (3 ml) and lithium iodide (53.1 mg, 0.40 mmol) was refluxed for 1 hour. After cooling, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) and crystallized (ethyl acetate/isopropyl ether) to give the title compound (90.3 mg, 65.3%) as a white crystal.

Workup

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

Sources & evidence

ORD record
ord-8ab5a19fc9564b5c9e290d5065ebc0d8
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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