Hippuric Acid → Azlactone

HRID 373363Notes

Reaction equation

[C:1]([OH:13])(=[O:12])[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C(OC(=O)C)(=O)C>>[C:6]1([C:4]2[O:13][C:1](=[O:12])[CH2:2][N:3]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 464Hippuric Acid

HCID 7918Acetic Anhydride

Product 1

HCID 65073Azlactone

Conditions

Temperature: 80 °C

Procedure

Separately, 2.08 g (0.0116 mol) of hippuric acid was added to 5.7 ml (0.0604 mol) of acetic anhydride and stirred at 80° C. for 10 minutes to obtain a solution of 2-phenyl-2-oxazolin-5-one. This solution was cooled to -20° C. and added with 1.65 g of anhydrous sodium acetate.

Sources & evidence

ORD record: ord-159af8364ca54eb88f45f42ccd1fc4cc
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162583

Reaction notes

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