Pyrrole → HCID 19790389, compound

HRID 893105Notes

Reaction equation

HRID 893105 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[NH:9][C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)=[C:11]([Cl:15])[C:12]=1[C:13]#[N:14].[CH2:24]([O:26][CH2:27]Cl)[CH3:25].N1C=CC=C1>CCCCCC.C(OCC)(=O)C.O1CCCC1>[Cl:7][C:8]1[N:9]([CH2:27][O:26][CH2:24][CH3:25])[C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)=[C:11]([Cl:15])[C:12]=1[C:13]#[N:14]

Participants

7

Reactant 4

HCID 8027PyrroleHCID 18523Chloromethyl ethyl etherHCID 19790384HCID 19790384, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19790389HCID 19790389, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of potassium tert-butoxide (0.62 g, 0.0055 mol) and tetrahydrofuran (50 mL) is added 2,4-dichloro-5-(3,4-dichlorophenyl)pyrrole-3-carbonitrile (1.3 g, 0.0043 mol) followed by chloromethyl ethyl ether (0.52 g, 0.0055 mol). After stirring the reaction mixture overnight, TLC (1:1 hexane/ethyl acetate shows no remaining starting pyrrole and the reaction is concentrated in vacuo. Addition of water to the residue affords a solid which is collected and dried to give the title compound as a brown solid (1.4 g, 90%, mp 106°-109° C.) which is indentified by IR and NMR spectral analyses.

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. additionAddition of water to the residue
  3. customaffords a solid which
  4. customis collected
  5. customdried

Sources & evidence

ORD record
ord-df03baedc5fa44dfa45608ecc6a8434f
Source dataset
uspto-grants-1992_06
Patent number
US05122615

Reaction notes

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