Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68585884, compound

HRID 17342Notes

Reaction equation

HRID 17342 reaction equation
[C:1]([C:4]1[C:9]([F:10])=[C:8](O)[C:7]([NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=[C:6]([C:18]#[N:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([C:4]1[C:9]([F:10])=[C:8]2[O:14][C:13]([CH:15]3[CH2:17][CH2:16]3)=[N:12][C:7]2=[C:6]([C:18]#[N:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86630836N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide

Product 1

HCID 68585884HCID 68585884, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide (I-81) (200 mg, 0.72 mmol) was dissolved in toluene (4 ml), pyridinium p-toluenesulfonate (40 mg, 0.14 mmol) was, added, followed by heating under reflux for 21 hours. After cooling to room temperature, this was diluted with ethyl acetate, washed with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, eluted with a mixed solvent of n-hexane/ethyl acetate (3:1, v/V) to obtain the entitled compound (133 mg, 71%) as a white solid.

Workup

  1. additionadded
  2. temperatureby heating
  3. temperatureunder reflux for 21 hours
  4. washwashed with water and saturated brine
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. washeluted with a mixed solvent of n-hexane/ethyl acetate (3:1

Sources & evidence

ORD record
ord-f2b23d306e474821bdd0557cf0e49d6d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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