Toluene → HCID 68584655, compound

HRID 17308Notes

Reaction equation

HRID 17308 reaction equation
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:20]([C:22]1[C:23]([N-:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[C:24]([OH:36])[C:25]([F:35])=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:27]=1[CH3:28])#[N:21]>C(OCC)(=O)C>[F:35][C:25]1[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:27]([CH3:28])[C:22]([C:20]#[N:21])=[C:23]2[C:24]=1[O:36][C:38]([CH:39]([CH3:41])[CH3:40])=[N:37]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 178428580HCID 178428580, compound

Product 1

HCID 68584655HCID 68584655, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Toluene (10 ml), p-toluenesulfonic acid monohydrate (5.3 mg, 28 μmol) were added to N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)isobutylamide (I-51) (87 mg, 279 μmol), followed by refluxing with a Dean-Stark condenser for 3.5 hours. During the course, p-toluenesulfonic acid monohydrate (5.3 mg, 28 μmol) was added. Alter cooled, ethyl acetate (50 ml) was added to the reaction liquid, the organic layer was successively washed with saturated sodium bicarbonate water (30 ml), saturated brine (30 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (82 mg, quant.) as a colorless solid.

Workup

  1. temperatureby refluxing with a Dean-Stark condenser for 3.5 hours
  2. temperatureAlter cooled
  3. washthe organic layer was successively washed with saturated sodium bicarbonate water (30 ml), saturated brine (30 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
  7. customto obtain the entitled compound (82 mg, quant.) as a colorless solid

Sources & evidence

ORD record
ord-7ba7df6db6064f089e827089d133a5d4
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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