Acetic Anhydride → 4-((2-Methyl-5-oxo-4(5H)-oxazolylidene)methyl)benzonitrile

HRID 7200

反応式

HRID 7200 の反応式
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[C:11]([NH:14][CH2:15][C:16]([OH:18])=[O:17])(=O)[CH3:12].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>CC(C)=O>[CH3:12][C:11]1[O:18][C:16](=[O:17])[C:15](=[CH:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)[N:14]=1

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 660424-CyanobenzaldehydeHCID 517045Sodium Acetate

生成物 1

HCID 3670804-((2-Methyl-5-oxo-4(5H)-oxazolylidene)methyl)benzonitrile

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

Acetone (80.0 l) was introduced into a mixture of 4-formylbenzonitrile (15.0 kg, 114.5 mol), N-acetylglycine (19.2 kg, 162.4 mol) and anhydrous sodium acetate (9.4 kg, 114.5 mol) followed by introduction, with stirring, of acetic anhydride (35.0 l, 370.5 mol). The reaction mixture was stirred under reflux for 1 h. The resulting thin yellow suspension was cooled to 50° C. and ice-water (200 l) was added as quickly as possible, with stirring and cooling. The mixture was stirred at 20° C. for another 1 h. To isolate the product, the yellow suspension was pressed onto a centrifuge and washed with deionized water (75 l), isopropanol (40 l) and methyl-tert-butylether (75 l). The product was dried under reduced pressure at 40° C. Yield 18.17 kg (85.7 mol, 75.2% of theory). M.p.: 192–193° C.; MS (DCl): m/z=213 [M+H+]; 1H-NMR (DMSO-d6): δ=2.42 (s, 3H), 7.30 (s, 1H), 7.96 (d, 2H), 8.33 (d, 2H).

後処理

  1. temperatureunder reflux for 1 h
  2. stirringwith stirring
  3. temperaturecooling
  4. stirringThe mixture was stirred at 20° C. for another 1 h
  5. customTo isolate the product
  6. washwashed with deionized water (75 l), isopropanol (40 l) and methyl-tert-butylether (75 l)
  7. customThe product was dried under reduced pressure at 40° C

出典と根拠

ORDレコード
ord-6c3f31a14b3b47a1ba8904aea201e513
出典データセット
uspto-grants-2006_08
特許番号
US07084250B2

関連ノート

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