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

HRID 7200

반응식

HRID 7200 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6c3f31a14b3b47a1ba8904aea201e513
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084250B2

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