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

HRID 7200

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-6c3f31a14b3b47a1ba8904aea201e513
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084250B2

Linked notes

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