Ethylene Glycol → HCID 57590527, compound

HRID 1783490Notes

Reaction equation

HRID 1783490 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22](I)[C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]1[CH:32]=[C:31]2[CH:33]=[CH:34][CH:35]=[C:36]([SH:37])[C:30]2=[CH:29][CH:28]=1.C(O)CO.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C.CO.C(Cl)Cl.[Cu]I>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22]([S:37][C:36]4[C:30]5[C:31](=[CH:32][CH:27]=[CH:28][CH:29]=5)[CH:33]=[CH:34][CH:35]=4)[C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 57590525HCID 57590525, compound

Product 1

HCID 57590527HCID 57590527, compoundYield 99.8%

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 4-(4-iodobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester (0.80 g, 1.73 mmol), 1-naphthylthiol (0.276 g, 1.73 mmol), CuI (0.066 g, 0.35 mmol), ethylene glycol (0.214 g, 3.45 mmol), and K2CO3(0.477 g, 3.45 mmol) in isopropanol was heated at 90° C. overnight, cooled, diluted with 20% MeOH in CH2Cl2 and filtered through a pad of silica gel. The filtrated was concentrated and purified by chromatography with 1-3% MeOH in CH2Cl2 to provide the title compound (0.856 g, 93%), characterized by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. filtrationfiltered through a pad of silica gel
  3. concentrationThe filtrated was concentrated
  4. custompurified by chromatography with 1-3% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f7800f338ea840ef9f35c02020278be5
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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