Water → 4,5-Dichloro-2-(3,4-dichlorophenyl)-1-(ethoxymethyl)pyrrole-3-carbonitrile

HRID 1033569

Reaction equation

HRID 1033569 reaction equation
[Cl:1][C:2]1[C:3]([C:16]#[N:17])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[NH:5][C:6]=1[Cl:7].CC(C)([O-])C.[K+].[CH2:24]([O:26][CH2:27]Cl)[CH3:25].O>O1CCCC1>[Cl:1][C:2]1[C:3]([C:16]#[N:17])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]([CH2:27][O:26][CH2:24][CH3:25])[C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 150101404,5-Dichloro-2-(3,4-dichlorophenyl)-1-(ethoxymethyl)pyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of 4,5-dichloro-2-(3,4-dichlorophenyl)pyrrole-3-carbonitrile (1.0 g, 0.003 mole) is dissolved in 10 mL of dry tetrahydrofuran. To this solution is added potassium t-butoxide (0.37 g, 0.0033 mole) followed by chloromethyl ethyl ether (0.312 g, 0.0033 mole). The mixture is stirred for about 1 hour at room temperature and then poured into a large volume of water precipitating the product. The white solid is collected and dried to give 1.0 g (91%) with mp 128°-130°.

Workup

  1. customThe white solid is collected
  2. customdried
  3. customto give 1.0 g (91%) with mp 128°-130°

Sources & evidence

ORD record
ord-ba7b38958b0b459d85a745bd4b393d4b
Source dataset
uspto-grants-1994_05
Patent number
US05310938

Linked notes

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