1,1'-Carbonyldiimidazole → Tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate

To a suspension of 1,1′-carbonyldiimidazole (1.783 g, 11.00 mmol) in anhydrous tetrahydrofuran (7 ml) was added tert-butyl carbazate (1.322 g, 10.00 mmol), and the mixture was stirred at room temperature for 30 min. A solution of 4-(aminomethyl)aniline (1.228 g, 10.05 mmol) in anhydrous tetrahydrofuran (3 ml) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under to reduced pressure, and ethyl acetate (50 ml) and water (50 ml) were added to the residue. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 90 g, ethyl acetate:hexane=7:3→8:2→9:1) to give tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate (2.180 g, 7.778 mmol, yield 77.8%) as a white solid.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. customThe solvent was evaporated under to reduced pressure, and ethyl acetate (50 ml) and water (50 ml)
3. additionwere added to the residue
4. stirringThe mixture was stirred
5. custompartitioned
6. extractionThe aqueous layer was extracted twice with ethyl acetate
7. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 90 g, ethyl acetate:hexane=7:3→8:2→9:1)

ORD record

ord-e93dafdb4e0e40c5b47cc4ffba687940

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2