Chloromethyl ethyl ether → HCID 18969613, compound

HRID 399032Notes

Reaction equation

HRID 399032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:30]([O:32][CH2:33]Cl)[CH3:31]>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:33][O:32][CH2:30][CH3:31])[C:10]([S:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)=[CH:11][C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 18969625HCID 18969625, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969613HCID 18969613, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(p-chlorophenyl)-5-[(3,4-dichlorophenyl)thio]pyrrole-3-carbonitrile (820 mg, 2.16 mmol) and potassium tert-butoxide (266 mg, 2.37 mmol) in tetrahydrofuran is stirred at room temperature for 30 minutes, treated with chloromethyl ethyl ether (225 mg, 2.37 mmol), stirred at room temperature for 4 hours, and diluted with water and ethyl acetate. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and extracts are combined, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a syrup. The syrup is crystallized from an ethyl acetate/hexanes solution to give the title product as a solid (780 mg, mp 95°-97° C.).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a syrup
  8. customThe syrup is crystallized from an ethyl acetate/hexanes solution

Sources & evidence

ORD record
ord-d6723ef480d248af98d59ef6d9237649
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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