3-Isoxazolamine, 5-(1,1-dimethylethyl)- → Pentanenitrile, 4,4-dimethyl-3-oxo-

HRID 128429

Reaction equation

HRID 128429 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4]N=1.NC1ON=C(C(C)(C)C)C=1>C(#N)C>[C:5]([CH2:6][C:2]#[N:1])(=[O:4])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 20956943-Tert-butyl-1,2-oxazol-5-amine

Product 1

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This invention relates to a method for optimizing the yield of 3-amino-5-(t-butyl)isoxazole over the yield of the isomeric 5-amino-3-(t-butyl)isoxazole. The method is carried out in a stepwise manner utilizing in a first step the reaction of a lower alkyl pivalate with acetonitrile in the presence of a base to yield pivalyl acetonitrile, which pivalyl acetonitrile is then reacted with hydroxylamine under carefully controlled conditions of pH to yield a preponderance of 3-amino-5-(t-butyl)isoxazole.

Sources & evidence

ORD record
ord-7a554b4c3abf445080b166ad1234b944
Source dataset
uspto-grants-1981_03
Patent number
US04259501

Linked notes

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