Hydrochloric Acid → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

4,4-dimethyl-3-oxopentanenitrile (3 g, 23.97 mmol) was dissolved in distilled water, stirred, and added with NaOH (1.06 g, 26.4 mmol) and NH2OH.HCl (1.83 g, 26.4 mmol). The reaction solution was stirred for about 30 minutes at room temperature. The reaction mixture was calibrated to yield pH in a range of 8 to 9 by adding an aqueous solution of 1 N NaOH, followed by further stirring for 10 hours or more at 50° C. The reaction mixture was washed 2 to 3 times with carbon tetrachloride, and aqueous layer was calibrated to yield pH in a range of 4 to 5 by adding concentrated HCl. The reaction mixture was further stirred for about 3 hours at 50° C. The reaction mixture was cooled to room temperature, and calibrated to yield pH 12 by adding an aqueous solution of 1 N NaOH. The resulting solid was filtered under reduced pressure, and washed with distilled water. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (2.6 g, 77%).

1. stirringThe reaction solution was stirred for about 30 minutes at room temperature
2. customto yield pH in a range of 8 to 9
3. stirringby further stirring for 10 hours or more at 50° C
4. washThe reaction mixture was washed 2 to 3 times with carbon tetrachloride, and aqueous layer
5. customto yield pH in a range of 4 to 5
6. stirringThe reaction mixture was further stirred for about 3 hours at 50° C
7. customto yield pH 12
8. filtrationThe resulting solid was filtered under reduced pressure
9. washwashed with distilled water
10. customThe filtered solid was dried
11. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

ORD record

ord-84edbd5213334ec58cd01af16cbfb370

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156852B2