Glycine → 4-((4-Fluorophenyl)methylene)-2-methyl-5(4H)-oxazolone

HRID 612504

Reaction equation

HRID 612504 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]([O-])(=O)[CH3:7].[Na+].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.O>C(OC(=O)C)(=O)C>[CH3:6][C:7]1[O:4][C:3](=[O:5])[C:2](=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[N:1]=1

Participants

6

Reactant 4

HCID 750GlycineHCID 962WaterHCID 680234-FluorobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 3670734-((4-Fluorophenyl)methylene)-2-methyl-5(4H)-oxazoloneYield 78.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

With stirring, 7.5 g (0.1 mol) of glycine with 6.2 g (0.075 mol) of anhydrous sodium acetate and 18.6 g (0.15 mol) of p-fluorobenzaldehyde in 60 ml of acetic anhydride are heated to 100° C. After 2 hours, the reaction is cooled and poured into water. The resulting precipitate is filtered off with suction and dried under reduced pressure. 12.1 g (59% of theory) of 2-methyl-4-(4-fluorobenzylidene)-oxazol-5-one of mp. 156° C. are obtained.

Workup

  1. temperaturethe reaction is cooled
  2. filtrationThe resulting precipitate is filtered off with suction
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-6a124d6a9c454b1db81f3ca950d6acaf
Source dataset
uspto-grants-1999_12
Patent number
US06004992

Linked notes

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