1-(1H-imidazole-1-carboximidoyl)-1H-imidazole → 2-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17443Notes

Reaction equation

HRID 17443 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18].[N:19]1(C(N2C=CN=C2)=N)C=CN=[CH:20]1>O1CCCC1>[NH2:19][C:20]1[O:8][C:7]2[C:2](=[C:3]([C:17]#[N:18])[C:4]([CH3:16])=[C:5]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[F:9])[N:1]=1

Participants

4

Reactant 2

HCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazoleHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 685859852-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (1.66 g, 6.86 mmol) and di(imidazol-1-yl)methanimine (2.821 g) were suspended in tetrahydrofuran (33 ml), and stirred under reflux under nitrogen atmosphere for 120 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The residue was fractionated with 10% methanol-containing chloroform and water. The organic layer was separated, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, and the solvent was evaporated away under reduced pressure. The residue was recrystallized form methanol to obtain the entitled compound (1.60 g, 87%) as a pale brown solid.

Workup

  1. temperatureunder reflux under nitrogen atmosphere for 120 hours
  2. customthe solvent was evaporated away under reduced pressure
  3. additioncontaining chloroform and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe residue was recrystallized form methanol

Sources & evidence

ORD record
ord-98ab37a38b804d2688562a7942c0e842
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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