Chloromethyl ethyl ether → HCID 18969620, compound

HRID 399033Notes

Reaction equation

HRID 399033 reaction equation
[Br:1][C:2]1[C:3]([C:23]#[N:24])=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[NH:5][C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1.CC(C)([O-])C.[K+].[CH2:31]([O:33][CH2:34]Cl)[CH3:32]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([C:23]#[N:24])=[C:4]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[N:5]([CH2:34][O:33][CH2:31][CH3:32])[C:6]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 18969587HCID 18969587, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969620HCID 18969620, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-2-(p-chlorophenyl)-5-[(3,4-dichlorophenyl)thio]pyrrole-3-carbonitrile (0.644 g, 1.40 mmol) and potassium tert-butoxide (0.173 g, 1.54 mmol) in tetrahydrofuran is stirred at room temperature for 30 minutes, treated with chloromethyl ethyl ether (0.16 mL, 1.54 mmol), stirred overnight at room temperature, diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a solid. The solid is recrystallized from an ethyl acetate/hexanes solution to give the title product as a white solid (0.554 g, mp 105°-107° C.).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a solid
  5. customThe solid is recrystallized from an ethyl acetate/hexanes solution

Sources & evidence

ORD record
ord-145886b7682f4479ae4ffdcbd5c87104
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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