(1Z)-2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride → 2-[3-(4-Chlorobenzoyl)-isoxazol-5-yl]propan-1-ol

HRID 638548Notes

Reaction equation

HRID 638548 reaction equation
[CH:1]1[C:6]([C:7](/[C:9](/Cl)=[N:10]/[OH:11])=[O:8])=[CH:5][CH:4]=[C:3]([Cl:13])[CH:2]=1>CC(C#C)CO>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:4]=[C:5]([CH:6]([CH3:1])[CH2:7][OH:8])[O:11][N:10]=2)=[O:8])=[CH:1][CH:2]=1

Participants

3

Reactant 1

HCID 9614280(1Z)-2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride

Product 1

HCID 135375952-[3-(4-Chlorobenzoyl)-isoxazol-5-yl]propan-1-olYield 254.7%

Reagents, catalysts & solvents 1

HCID 1024422-Methylbut-3-yn-1-olSolvent

Procedure

A solution of 8.7 g of 4-chlorophenylglyoxylohydroxamyl chloride in 16.7 g of 2-methyl-3-butyn-1-ol was refluxed under N2 for 3 hours. The resulting mixture was concentrated under reduced pressure to give 13.5 g of an oil. This material was purified by high pressure liquid chromatography with 5% ethyl acetate/CH2Cl2 used as an eluent to give 6.3 g (59%) of an oil which solidified on standing, m.p. 49°-51°.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64a4d8cd70a24d968ca2a4260f41dddc
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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