Hydrochloric Acid → HCID 11475621, compound

HRID 2384375Notes

Reaction equation

HRID 2384375 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])CCC.N1C(C)=CC(C)=[CH:33][C:32]=1[CH3:39].[I-].[Li+].Cl>>[F:22][C:20]([F:23])([F:21])[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:32]([CH3:39])[CH3:33])[CH:7]=[CH:8][C:9]=2[OH:29])[CH:15]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 17860194HCID 17860194, compound

Product 1

HCID 11475621HCID 11475621, compoundYield 65.3%

Procedure

A mixture of 5-butyryl-N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-benzamide (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-619f34e905184ff785d299ddf47c5dee
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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