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

To a suspension of cyanopinacolone (75.102 g) in a mixture of anhydrous toluene (150 ml) and anhydrous methanol (26.7 ml) is introduced gaseous hydrogen chloride (26.3 g) with cooling at 5° to 10° C. and stirring, and the whole mixture is allowed to stand at 10° to 12° C. for 23 hours. To the reaction mixture is dropwise added anhydrous methanol (750 ml), then triethylamine (185.178 g) with cooling and stirring to make a complete solution. The reaction mixture is treated with hydroxylamine sulfate (51.704 g) and stirred at 50° C. for 2 hours. Then, conc. hydrochloric acid (112.629 g) is dropwise added to the mixture, which is stirred at 50° C. for 1 hour. After evaporating the solvent under reduced pressure from the reaction mixture, the residue is made alkaline with 48% aqueous sodium hydroxide with cooling, and the aqueous solution is shaken with toluene. The organic layer is washed with water, subjected to azeotropic distillation under atmospheric pressure, and evaporated to dryness to remove the solvent, whereby 3-amino-5-t-butylisoxazole (79.480 g) is obtained. Melting point is 106° to 109° C. Yield is 94.5%.

1. temperaturewith cooling at 5° to 10° C.
2. stirringstirring
3. stirringstirred at 50° C. for 2 hours
4. stirringis stirred at 50° C. for 1 hour
5. customAfter evaporating the solvent under reduced pressure from the reaction mixture
6. temperaturewith cooling
7. stirringthe aqueous solution is shaken with toluene
8. washThe organic layer is washed with water
9. distillationsubjected to azeotropic distillation under atmospheric pressure
10. customevaporated to dryness
11. customto remove the solvent

ORD record

ord-e0243889b3314b86866a469416fc81b0

Source dataset

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04200757