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

HRID 17443ノート

反応式

HRID 17443 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98ab37a38b804d2688562a7942c0e842
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…