반응 #44933

ord-71dc152e54a64201b2053bf3e0715fa6

반응 방정식

[Cl][Sn][Cl]
tin(II) chloride
Nc1ccc(S(N)(=O)=O)cc1
sulfanilamide
O=N[O-].[Na+]
sodium nitrite
Cl
hydrochloric acid
Cl.NNc1ccc(S(N)(=O)=O)cc1
4-sulfonamidophenylhydrazine hydrochloride
수율 55.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

a Celecoxib Analog: Compound 30c, 3-[1-{p-(Sulfonamido)phenyl}-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid., was synthesized by the method depicted in FIG. 2. Briefly, 4′-methylacetophenone and succinnic hydride were reacted in the presence of lithium diisopropanolamine (LDA) and tetrahydrofuran (THF) for 1 hour at −78° C. to produce p-tolyl-4,6-dioxohexanoic acid as a white solid (66% yield). Also sulfanilamide has reacted with sodium nitrite (NaNO2) and concentrated hydrochloric acid at 0-4° C. for 30 minutes, after which tin(II) chloride (SnCl2) was added and the reaction allowed to continue for an additional 4 hours at 0° C. to produce 4-sulfonamidophenylhydrazine hydrochloride as a pale yellow solid (55% yield). The 4,6,dioxo-6-p-tolylhexanoic acid and the 4-sulfonamidophenylhydrazine hydrochloride were then complexed for 16 hours at room temperature in the presence of triethanolamine (TEA) in methanol to produce Compound 30c as a yellow solid (76% yield).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07736624B2uspto-grants-2010_06