Aniline → HCID 59398537, compound

HRID 2070042Notes

Reaction equation

HRID 2070042 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([CH2:16][CH2:17][CH2:18][OH:19])[CH:7]=1)=[O:4].NC1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]([F:20])([F:21])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:13])([F:15])[F:14])[CH:9]=[C:8]([CH2:16][CH2:17][CH:18]=[O:19])[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 6115AnilineHCID 159087TriacetoxyperiodinaneHCID 86643169HCID 86643169, compound

Product 1

HCID 59398537HCID 59398537, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoro-N-[3-(3-hydroxypropyl)-5-(trifluoromethyl)phenyl]acetamide (240 mg, 0.76 mmol) prepared by a method similar to that in the above “intermediate aniline: Synthesis 6” was dissolved in dichloromethane (5 mL), and Dess-Martin periodinane (355 mg, 0.84 mmol) was added thereto under ice-cooling. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 14 hours. The reaction solution was partitioned between a saturated sodium bicarbonate solution (30 mL) and ethyl acetate (50 mL). The organic layer was washed with saturated brine and then concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=1:1) to give 2,2,2-trifluoro-N-[3-(3-oxopropyl)-5-(trifluoromethyl)phenyl]acetamide (100 mg, 42%) as a yellow oil.

Workup

  1. customSynthesis 6”
  2. temperatureunder ice-cooling
  3. customThe reaction solution was partitioned between a saturated sodium bicarbonate solution (30 mL) and ethyl acetate (50 mL)
  4. washThe organic layer was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-04c5f66270a646df87f9f55501744cfa
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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