Diethylene Glycol Monomethyl Ether → HCID 58585875, compound

HRID 1297651Notes

Reaction equation

HRID 1297651 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[H-].[Na+].[I:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][C:16]([C:22]#[N:23])=[CH:15]2>CN(C=O)C>[I:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][C:16]([C:22]#[N:23])=[C:15]2[O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 68824722HCID 68824722, compound

Product 1

HCID 58585875HCID 58585875, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of diethylene glycol monomethyl ether (0.75 mL, 6.4 mmol) in DMF (10 mL) was added sodium hydride (0.26 g, 6.4 mmol). After stirring at room temperature for 30 min, 6-iodo-quinoline-3-carbonitrile (example 14c) (1.0 g, 3.18 mmol) was added to the mixture. After further stirring at room temperature for 30 min, ice water was slowly added to the reaction. The reaction was extracted with methylene chloride. The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-45% ethyl acetate in hexanes in 30 min) afforded 6-iodo-4-[2-(2-methoxy-ethoxy)-ethoxy]-quinoline-3-carbonitrile (0.59 g, 46%) as a light yellow solid. LC-MS m/e 399 (MH+).

Workup

  1. stirringAfter further stirring at room temperature for 30 min
  2. extractionThe reaction was extracted with methylene chloride
  3. washThe combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23cc61a548044c9eb7f686fc66e7927d
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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