Sodium Iodide → HCID 18969589, compound

HRID 399035Notes

Reaction equation

HRID 399035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:23]([F:26])([F:25])[F:24])=[C:11]([S:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[I-].[Na+].[CH2:35]([O:37][CH2:38]Cl)[CH3:36]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:38][O:37][CH2:35][CH3:36])[C:10]([C:23]([F:25])([F:24])[F:26])=[C:11]([S:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 18523Chloromethyl ethyl etherHCID 18969631HCID 18969631, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969589HCID 18969589, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(p-chlorophenyl)-4-[(p-chlorophenyl)thio]-5-(trifluoromethyl)pyrrole-3-carbonitrile (1.7 g, 4.1 mmol), potassium tert-butoxide (0.5 g, 4.5 mmol) and sodium iodide (0.67 g, 4.5 mmol) in tetrahydrofuran is stirred at room temperature for 15 minutes, treated with chloromethyl ethyl ether (0.425 g, 4.5 mmol), stirred at room temperature for 6 hours and poured into water. The aqueous mixture is extracted with diethyl ether. The organic extract is washed sequentially with a 2 molar potassium hydroxide solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an oil. A mixture of the oil in hexanes is stored overnight at room temperature and filtered to obtain the title product as a white solid (1.25 g, mp 98°-100° C.).

Workup

  1. stirringstirred at room temperature for 6 hours
  2. extractionThe aqueous mixture is extracted with diethyl ether
  3. extractionThe organic extract
  4. washis washed sequentially with a 2 molar potassium hydroxide solution and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an oil
  8. waitis stored overnight at room temperature
  9. filtrationfiltered

Sources & evidence

ORD record
ord-689c62f9e71e4e28a87a60e4fcff18f8
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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