Ethylene Glycol → HCID 59304173, compound

HRID 1711425Notes

Reaction equation

HRID 1711425 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.[CH:14]1[CH:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([SH:24])[C:17]2=[CH:16][CH:15]=1.C(O)CO>C(O)(C)C.CO.C(Cl)Cl.[Cu]I>[C:23]1([S:24][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[NH:4][N:3]=2)[C:17]2[C:18](=[CH:19][CH:14]=[CH:15][CH:16]=2)[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 3

HCID 174Ethylene GlycolHCID 682591-NaphthalenethiolHCID 178526495HCID 178526495, compound

Product 1

HCID 59304173HCID 59304173, compoundYield 49%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-iodo-5-nitro-1H-indazole (10.00 g, 34.60 mmol), 1-naphthylthiol (5.54 g, 34.60 mmol), CuI (0.659 g, 3.46 mmol) and ethylene glycol (4.30 g, 69.20 mmol) in isopropanol was heated at 90° C. under nitrogen overnight, cooled, diluted with 30% MeOH in CH2Cl2, and filtered through a pad of silica gel. The filtrate was concentrated in vacuo. The concentrate was purified by chromatography with 1% MeOH in CH2Cl2 to provide the title compound, 5.5 g (49% yield), characterized by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. filtrationfiltered through a pad of silica gel
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe concentrate was purified by chromatography with 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-767263041c1d457185fb847f72154e3d
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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