Ethylene Glycol → HCID 178509630, compound

HRID 1254028Notes

Reaction equation

HRID 1254028 reaction equation
C([O-])([O-])=O.[K+].[K+].I[C:8]1[NH:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1.C(O)CO>CCOC(C)=O.[Cu]I.CC(O)C>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34][C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 66986216HCID 66986216, compound

Product 1

HCID 178509630HCID 178509630, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

CuI (20 mg, 0.104 mmol), K2CO3 (573 mg, 4.15 mmol), the product of Step 2 (770 mg, 2.0 mmol), and 4-chlorobenzenethiol (330 mg, 2.2 mmol) were added to a flask, which was flushed with N2. 2-Propanol (8 mL) and ethylene glycol (0.23 mL, 4.15 mmol) were added. The reaction mixture was heated at 80° C. for 24 h. Then the reaction was diluted with EtOAc, filtered, concentrated, and the residue was subject to silica column chromatography (5-25% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CD3OD): 8.08 (m, 1H), 8.01 (d, 2H), 7.78 (d, 2H), 7.47 (m, 4H), 7.24 (d, 2H), 7.17 (d, 2H). LCMS: m/z 388.0 (M+H)+.

Workup

  1. customwhich was flushed with N2
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8d83cfcf9a1340c3bd084f9fa3cbb716
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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