Iodoethane → HCID 18424230, compound

HRID 1606151Notes

Reaction equation

HRID 1606151 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[NH:11][C:10]([CH2:12][C:13]#[N:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24].CC(CC)=[O:28]>O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:7]2[N:11]([CH2:23][CH3:24])[C:10]([CH2:12][C:13]#[N:14])=[CH:9][CH:8]=2)=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 18424368HCID 18424368, compound

Product 1

HCID 18424230HCID 18424230, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 24.4 g. (0.1 mole) 5-(p-chlorobenzyl)-pyrrole-2-acetonitrile, 41.7 g. (0.3 mole) of potassium carbonate and 16.1 g. (0.105 mole) of ethyl iodide in 300 ml. of methylethylketone is refluxed overnight. The reaction mixture is then poured into water and extracted with chloroform. The organic solutions are combined, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue is crystallized from 2-propanol to give about 13 g. of crude solid. The solid is sublimed overnight at 140°C. and 0.025 mm. Hg. The sublimate is successively recrystallized from 2-propanol, benzene and hexane to give 5-(p-chlorobenzoyl)-1-ethylpyrrole-2-acetonitrile as a white solid, m.p. 145°-147°C.

Workup

  1. additionA mixture of 24.4 g
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe residue is crystallized from 2-propanol
  6. customto give about 13 g
  7. customThe sublimate is successively recrystallized from 2-propanol, benzene and hexane

Sources & evidence

ORD record
ord-0e829ed7eca4497780d561c559bd5b7b
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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