Iodoethane → 2-(3-Ethoxyphenyl)-5H-[1,2,4]triazolo[5,1-a]isoindole

HRID 436199Notes

Reaction equation

HRID 436199 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:19]=[C:11]3[C:12]4[C:17]([CH2:18][N:10]3[N:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:6][CH:7]=1.[O-][CH2:21][CH3:22].[Na+].C(I)C>C(O)C>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:19]=[C:11]3[C:12]4[C:17]([CH2:18][N:10]3[N:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:6][CH:7]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 2723922Sodium ethoxideHCID 21455283HCID 21455283, compound

Product 1

HCID 1344512-(3-Ethoxyphenyl)-5H-[1,2,4]triazolo[5,1-a]isoindoleYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(3-Hydroxyphenyl)-5H-s-triazolo[5,1-a] isoindole (1.25 g, 0.05 mole) is added to 20 ml of ethanol containing one equivalent proportion of sodium ethoxide. To this mixture is added 0.49 ml (0.06 mole) of ethyl iodide in 5 ml of ethanol. After stirring for one hour at room temperature, a further amount of 0.49 ml of ethyl iodide is added. After refluxing for one hour the solvent is distilled off and the residue is washed with water and extracted with dichloromethane. Evaporation of the solvent and crystallization of the residue from ethanol gives 1 g (73%) of the title product, m.p. 166°-7° C.

Workup

  1. temperatureAfter refluxing for one hour the solvent
  2. distillationis distilled off
  3. washthe residue is washed with water
  4. extractionextracted with dichloromethane
  5. customEvaporation of the solvent and crystallization of the residue from ethanol

Sources & evidence

ORD record
ord-410221a369704c02b3a1f49c9d41d587
Source dataset
uspto-grants-1977_02
Patent number
US04007276

Reaction notes

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