Tert-Butylamine → HCID 13026937, compound

2-Hydroxyisophthalic acid (1.82 g) and N,N'-dicyclohexylcarbodiimide (2.17 g) were dissolved together in dry pyridine (30 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was then treated with dry tert-butylamine (5 ml), and the mixture was stirred at 60° C. for 20 hours. The solvents were removed in vacuo, and the residue was treated with saturated aqueous sodium bicarbonate solution (50 ml). The mixture was stirred for 15 minutes. The insoluble N,N'-dicyclohexylurea was then removed by filtration and the resulting filtrate was treated with charcoal and filtered again. The filtrate was then acidified by treatment with concentrated hydrochloric acid to give a white solid which was filtered off and recrystallized from a mixture of petroleum ether (b.p. 60°-80° C.) and benzene to give 3-tert-butylcarbamoylsalicylic acid (1.2 g), m.p. 191°-195° C.

1. stirringthe mixture was stirred at 60° C. for 20 hours
2. customThe solvents were removed in vacuo
3. additionthe residue was treated with saturated aqueous sodium bicarbonate solution (50 ml)
4. stirringThe mixture was stirred for 15 minutes
5. customThe insoluble N,N'-dicyclohexylurea was then removed by filtration
6. additionthe resulting filtrate was treated with charcoal
7. filtrationfiltered again
8. customto give a white solid which
9. filtrationwas filtered off
10. customrecrystallized from a mixture of petroleum ether (b.p. 60°-80° C.) and benzene

ORD record

ord-472a118abd0a4677a346f32ff2ce192e

Source dataset

uspto-grants-1979_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04146631