Ethylenediaminetetraacetic Acid → 5-Acetyl-2-aminobenzenesulfonamide

온도

-78 °C

To a solution of ethylvinylether (5.8 ml, 60 mmol) in dry THF (50 ml) at −78° C. was added t-BuLi (1.7 M in pentane, 25 ml, 40 mmol) and the yellow mixture was stirred for 1 h at −78° C. The cooling bath was removed and the mixture was warmed slowly to 0° C. and stirred for another 30 min. The mixture was recooled to −78° C. and a solution of ZnCl2 (2M in THF, 20 ml, 40 mmol) was added slowly and the cooling bath was removed and warmed to 20° C. 5-Iodo-2-aminobenzenesulfonamide (see compound 37) (1.8 g, 6 mmol) and Pd(PPh3)4 (0.2 g, 3 mol %) was added and the mixture was refluxed for 6 h. The THF was evaporated and the residue was boiled in 1 M hydrochloric acid (30 ml) and MeOH (30 ml) for 30 min. EDTA (14.6 g, 50 mmol) was added and made slightly basic (pH=8-9) with 1 M NaOH followed by extraction with EtOAc (3×150 ml), drying (Na2SO4) and evaporation of the solvent gave a brown solid. Trituration with n-hexane gave 0.95 g (74%) of 5-acetyl-2-aminobenzenesulfonamide as off-white powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 224-226° C. (decomp).

1. customThe cooling bath was removed
2. temperaturethe mixture was warmed slowly to 0° C.
3. stirringstirred for another 30 min
4. customwas recooled to −78° C.
5. customthe cooling bath was removed
6. temperaturewarmed to 20° C
7. temperaturethe mixture was refluxed for 6 h
8. customThe THF was evaporated
9. waitMeOH (30 ml) for 30 min
10. extractionfollowed by extraction with EtOAc (3×150 ml)
11. customdrying
12. custom(Na2SO4) and evaporation of the solvent
13. customgave a brown solid

ORD 기록

ord-d882de079fe840589a1adccd40227bc2

출처 데이터셋

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06943159B1