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

HRID 638549Notes

Reaction equation

HRID 638549 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>C(O)CCCC#C>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][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 135375964-[3-(4-Chlorobenzoyl)isoxazol-5-yl]butan-1-olYield 233.8%

Reagents, catalysts & solvents 1

HCID 702345-Hexyn-1-olSolvent

Procedure

A solution of 12 g of 4-chlorophenylglyoxylohydroxamyl chloride in 30 g of 5-hexyn-1-ol was refluxed under N2 for 2.5 hours. Concentration of the product on a rotovapor under high vacuum gave 18 g of an oil. Purification by high pressure liquid chromatography with 5% ethyl acetate/CH2Cl2 used as a eluent yielded 12.0 g (78%) of an oil which solidified on standing, m.p. 48°-51°.

Sources & evidence

ORD record
ord-e48f038bb28b4cdf81179d4a2552a0ba
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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