Dimethylformamide → 5(2H)-Oxazolone, 4-(4-chlorophenyl)-2-(trifluoromethyl)-

HRID 2400142

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](NCC(O)=O)=[CH:4][CH:3]=1.CN(C)C=[O:16].P(Cl)(Cl)Cl.[F:22][C:23]([F:28])([F:27])[C:24](Cl)=[O:25].[C:29](#[N:31])[CH3:30]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:29]2[C:30](=[O:16])[O:25][CH:24]([C:23]([F:28])([F:27])[F:22])[N:31]=2)=[CH:6][CH:7]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 6342Acetonitrile

HCID 24387Phosphorus trichloride

HCID 61106Trifluoroacetyl chloride

HCID 2307172-((4-Chlorophenyl)amino)acetic acid

Product 1

HCID 110652915(2H)-Oxazolone, 4-(4-chlorophenyl)-2-(trifluoromethyl)-

Procedure

A solution of p-chlorophenylglycine (46.9 g, 0.25 mole) in a mixture of acetonitrile, xylenes and dimethyl formamide (74.8 w/w%, 24.9 w/w% and 0.3 w/w%, respectively) is treated sequentially with PCl3 (21.3 g, 0.155 mole) and trifluoroacetyl chloride (34.8 g, 0.26 mole), held at 40° C. for 0.5 hour, heated at 60° -65° C. for 8 hours and allowed to cool to room temperature. The title product is obtained in quantitative yield by HPLC analysis.

Workup

temperatureheated at 60° -65° C. for 8 hours

Sources & evidence

ORD record: ord-6e69ef7220c84e688f426d9d2773d60b
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05453508

Linked notes

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