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

HRID 1436439노트

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HRID 1436439 반응식
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

참가 물질

4

반응물 2

HCID 713FormamideHCID 986544-(Bromoacetyl)benzonitrile

생성물 1

HCID 223795804-(Oxazol-4-yl)benzonitrile수율 17%

시약·촉매·용매 1

HCID 962Water용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac8d02057f434e9dad91f92bbdd277bd
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618990B2

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