197776-00-4

Basic information

• Product Name: N,O-di(phenoxycarbonyl)-5-chlorooxindole
• Synonyms: N,O-di(phenoxycarbonyl)-5-chlorooxindole
• CAS NO: 197776-00-4
• Molecular Formula: C₂₂H₁₄ClNO₅
• Molecular Weight: 409
• Mol File: 197776-00-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,O-di(phenoxycarbonyl)-5-chlorooxindole(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-di(phenoxycarbonyl)-5-chlorooxindole(197776-00-4)
• EPA Substance Registry System: N,O-di(phenoxycarbonyl)-5-chlorooxindole(197776-00-4)

Safety Data

• Hazardous Substances Data: 197776-00-4(Hazardous Substances Data)

Upstream product

• 17630-75-0 5-chloro-indolin-2-one 
• 1885-14-9 phenyl chloroformate 
• 1351706-37-0 N-(2-iodo-4-chlorophenyl)-4-methylbenzenesulfonamide 

Downstream Products

• 197776-03-7 5-chloro-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 
• 120210-48-2 tenidap 
• 255712-76-6 5-chloro-2-methoxycarbonyloxy-indole-1-carboxylic acid phenyl ester 
• 301779-72-6 5-chloro-2-ethoxycarbonyloxy-indole-1-carboxylic acid phenyl ester 
• 301700-19-6 2-benzyloxycarbonyloxy-5-chloro-indole-1-carboxylic acid phenyl ester 
• 1355680-17-9 5-chloro-1-[(4-phenylpiperazin-1-yl)carbonyl]-1,3-dihydro-2H-indol-2-one 
• 1355680-14-6 N-benzyl-5-chloro-N-methyl-2-oxo-2,3-dihydro-1H-indole-1-carboxamide 
• 1355680-16-8 N-benzyl-5-chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide 
• 255712-65-3 5-chloro-1-phenoxycarbonyl-2-(thenoyloxy)indole 
• 255712-72-2 (Z)-5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 
• 17630-75-0 5-chloro-indolin-2-one 

Relevant articles and documents

Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs

The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically active compounds containing the oxindole pharmaco-phore.

Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles

Two protocols have been developed for the synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles starting from the corresponding N,O-diacyl derivatives obtained by treatment of 2-oxindoles with chloroformic acid esters and triethylamine. Th

New practical synthesis of tenidap

The development of a new, practical synthesis to tenidap is described. N,O-Dialkoxy(aryloxy)carbonylation of 5-chloro-2-oxo-2,3-dihydroindole, followed by removal of the O-alkoxy-(aryloxy)carbonyl group gave 1-[alkoxy(aryloxy)carbonyl]-5-chloro-2-oxo-2,3-dihydroindoles in good yields. The latter compounds were thenoylated in the 3-position. The role of DMAP in the acylation reaction is discussed. The structures of the thenoylated products and their enolate salts were investigated both in solution and solid phases. Ammonolysis of 5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3- dihydroindole afforded the corresponding 1-carbamoyl derivative (tenidap) in high yield. The corresponding 1-ethoxy- and 1-methoxycarbonyl derivatives could not be similarly transformed to tenidap; loss of the alkoxycarbonyl moiety occurred instead of carbamoylation.