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Hippuric Acid → Oxazolone

HRID 403526
Notes
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Reaction equation

HRID 403526 reaction equation
[C:1]([NH:9][CH2:10][C:11]([OH:13])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:16][CH:17](OCC)OCC)[CH3:15].C(OC(=O)C)(=O)C>CN(C1C=CN=CC=1)C>[CH2:14]([O:16]/[CH:17]=[C:10]1\[N:9]=[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:13][C:11]\1=[O:12])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 464Hippuric AcidHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformate

Product 1

HCID 1712094OxazoloneYield 47%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-benzamidoacetic acid (2.5 g, 13.8 mmol), DMAP (0.017 g, 0.138 mmol) and triethoxymethane (2.3 ml, 13.8 mmol), was added acetic anhydride (2.6 ml, 27.6 mmol). The mixture was heated to 140° C. for 30 min. The solvent was removed in vacuo and purification by silica gel chromatography (0-30% ethyl acetate in hexanes) gave 1.4 g (47%) of (Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one as an orange solid. 1H NMR (400 MHz, CDCl3) 8.09-8.04 (m, 2H), 7.56-7.51 (m, 1H), 7.50-7.43 (m, 2H), 7.35 (s, 1H), 4.43 (q, 2H), 1.49 (t, 3H).

Workup

  1. customThe solvent was removed in vacuo and purification by silica gel chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7ae4bcaa99724a8cb02a13fcc760c0e4
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748442B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes