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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 7-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17354
Notes
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Reaction equation

HRID 17354 reaction equation
[C:1]([C:3]1[C:4]([CH3:25])=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]([F:18])=[C:7]([OH:17])[C:8]=1[NH:9][C:10](=O)[C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])#[N: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>[F:18][C:6]1[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]([C:1]#[N:2])=[C:8]2[C:7]=1[O:17][C:10]([C:11]([CH3:14])([CH3:15])[CH2:12][OH:13])=[N:9]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86630840N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 685859577-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1′-biphenyl]-4-yl)-3-hydroxy-2,2-dimethylpropanamide (I-98) (184 mg, 0.54 mmol) was dissolved in toluene (3.7 ml), pyridinium p-toluenesulfonate (34 mg, 0.13 mmol) was added, followed by stirring under heat for 15 hours. After cooling to room temperature, this was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution 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 recrystallized and purified with diisopropyl ether/ethyl acetate to obtain the entitled compound (118.6 mg, 68%) as a white solid.

Workup

  1. temperatureunder heat for 15 hours
  2. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was recrystallized
  6. custompurified with diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-12851e62832341b3919bbaae660a156f
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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