Triethylamine → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

HRID 127716

Reaction equation

HRID 127716 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([N:12](CC)CC)C.S(O)(O)(=O)=O.NO>O>[NH2:9][C:8]1[CH:7]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[O:6][N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-Yield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of pivaloylacetonitrile (12.52 g) and triethylamine (11.27 g) in water (200 ml) is stirred and mixed with hydroxylamine sulfate (9.03 g). pH 8.22. The reaction mixture is treated as in Example 2 to give 3-amino-5-t-butylisoxazole (11.45 g; yield, 81.7%).

Workup

  1. additionThe reaction mixture is treated as in Example 2

Sources & evidence

ORD record
ord-d73c023895844ceaa0b5ec960b928bde
Source dataset
uspto-grants-1981_03
Patent number
US04256899

Linked notes

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