Formamide → 4-(Oxazol-4-yl)benzonitrile

HRID 1436439ノート

反応式

HRID 1436439 の反応式
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[CH:13]([NH2:15])=[O:14]>O>[O:14]1[CH:2]=[C:3]([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[N:15]=[CH:13]1

参加物

4

反応物 2

HCID 713FormamideHCID 986544-(Bromoacetyl)benzonitrile

生成物 1

HCID 223795804-(Oxazol-4-yl)benzonitrile収率 17%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

4-(2-Bromo-acetyl)-benzonitrile (1.2 g, 5.4 mmol) was dissolved in formamide (10 mL) and heated to 110° C. for 72 h. The mixture was cooled, diluted with water and extracted five times with methylene chloride. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (5%-10% acetone in hexane) afforded 4-(1,3-oxazol-4-yl)benzonitrile (0.16 g, 17%) as a white solid. Analytical HPLC: purity 100% at 270 nm, 6.8 min; 100% at 210-370 nm, 6.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

後処理

  1. temperatureThe mixture was cooled
  2. extractionextracted five times with methylene chloride
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ac8d02057f434e9dad91f92bbdd277bd
出典データセット
uspto-grants-2009_11
特許番号
US07618990B2

反応ノート

読み込み中…