Chloroform → HCID 131720054, compound

A solution of t-butyl-p-nitrophenyl carbonate (10 g; 0.0418 mole) in CHCl3 (400 ml) was added to a solution of diethylenetriamine (45 ml; 0.0417 mole) in CHCl3 (250 ml) at 0° C. over a period of 3 h. The reaction mixture was stirred overnight at room temperature. The precipitate that appeared was filtered and washed in CHCl3. The solvent was evaporated, first under reduced pressure with a water-aspirator, then with an oil-pump (0.05 mmHg; 50° C.). The residue was dissolved in a mixture ethylacetate (50 ml)/H2O (50 ml) and the solution was acidified to pH 4 with HCl 4N, extracted with ethylacetate (3×50 ml). The aqueous solution was adjusted to pH 9 with NaOH 2N and extracted with ethylacetate (3×50 ml). The aqueous phase was adjusted to pH 11.5 and extracted with ethylacetate (10×50 ml). The combined organic phases of the last extraction were evaporated under reduced pressure and the resulting oil was dissolved in water (50 ml) and acidified to pH 5. Evaporation of water yielded a slightly yellow solid, which was thoroughly washed with ether (yield: 6.41 g; 55%). 1H-NMR (D2O): 6 (ppm): 1.4 (s, 9H); 3.0 (t, 2H); 3.3 (s broad, 4H); 3.4 (t, 2H)

1. filtrationThe precipitate that appeared was filtered
2. washwashed in CHCl3
3. customThe solvent was evaporated, first under reduced pressure with a water-aspirator
4. customwith an oil-pump (0.05 mmHg; 50° C.)
5. dissolutionThe residue was dissolved in a mixture ethylacetate (50 ml)/H2O (50 ml)
6. extractionextracted with ethylacetate (3×50 ml)
7. extractionextracted with ethylacetate (3×50 ml)
8. extractionextracted with ethylacetate (10×50 ml)
9. extractionThe combined organic phases of the last extraction
10. customwere evaporated under reduced pressure
11. dissolutionthe resulting oil was dissolved in water (50 ml)
12. customEvaporation of water
13. customyielded a slightly yellow solid, which
14. washwas thoroughly washed with ether (yield: 6.41 g; 55%)

ORD record

ord-cf06d4561b8b4cbe8323c20fe034bb85

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05641625