4-acetyl-N,N-dibenzylbenzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】44957

【品名】4-acetyl-N,N-dibenzylbenzenesulfonamide

【CA登记号】

【分子式】C₂₂H₂₁NO₃S

【分子量】379.47968

【元素组成】C 69.63% H 5.58% N 3.69% O 12.65% S 8.45%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

In an alternative procedure, sodium 4-acetylbenzenesulfonate (IV) was refluxed with POCl3 and subsequently treated with dibenzylamine to afford sulfonamide (V). Bromination of (V) in chloroform yielded the bromo ketone (VI), which was hydrolyzed to phenacyl alcohol (VII) by treatment with ethanolic betaine, followed by aqueous NaHCO3. Addition of 4-fluorophenyl isocyanate (VIII) to (VII) and then cyclization in refluxing HOAc yielded the oxazolone (IX). Final debenzylation was achieved with concentrated H2SO4 to give the target sulfonamide.

参考文献中间体

合成目标

【1】 Godessart, N.; Crespo, M.I.; Puig, C.; et al.; Synthesis and biological evaluation of 3,4-diaryloxazolones: A new class of orally active cyclooxygenase-2 inhibitors. J Med Chem 2000, 43, 2, 214.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	44956	sodium 4-acetylbenzenesulfonate	61827-67-6	C₈H₇NaO₄S	详情	详情
(V)	44957	4-acetyl-N,N-dibenzylbenzenesulfonamide		C₂₂H₂₁NO₃S	详情	详情
(VI)	44958	N,N-dibenzyl-4-(2-bromoacetyl)benzenesulfonamide		C₂₂H₂₀BrNO₃S	详情	详情
(VII)	44959	N,N-dibenzyl-4-glycoloylbenzenesulfonamide		C₂₂H₂₁NO₄S	详情	详情
(VIII)	17977	1-Fluoro-4-isocyanatobenzene; 4-Fluorophenyl isocyanate	1195-45-5	C₇H₄FNO	详情	详情
(IX)	44960	N,N-dibenzyl-4-[3-(4-fluorophenyl)-2-oxo-2,3-dihydro-1,3-oxazol-4-yl]benzenesulfonamide		C₂₉H₂₃FN₂O₄S	详情	详情

Extended Information