Iodoethane → L 11204

HRID 616692Notes

Reaction equation

HRID 616692 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:20]=[C:11]3[C:12]4[C:17]([CH2:18][CH2:19][N:10]3[N:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:6][CH:7]=1.[O-][CH2:22][CH3:23].[Na+].C(I)C>C(O)C>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:20]=[C:11]3[C:12]4[C:17]([CH2:18][CH2:19][N:10]3[N:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:6][CH:7]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 1344013-(5,6-Dihydro[1,2,4]triazolo[5,1-a]isoquinolin-2-yl)phenolHCID 2723922Sodium ethoxide

Product 1

HCID 119282L 11204

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(3-Hydroxyphenyl)-5,6-dihydro-s-triazolo-[5,1-a]isoquinoline (3.95 g.) is added to 60 ml. of ethanol containing one equivalent proportion of sodium ethoxide. To this mixture is added 1.57 ml. of ethyl iodide in 15 ml. of ethanol. After stirring for one hour at room temperature, a further 1.57 ml. of ethyl iodide is added and the mixture is refluxed for 18 hours. 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 3.87 g. of the title product; m.p. 102°-3° C.

Workup

  1. additionTo this mixture is added 1.57 ml
  2. temperaturethe mixture is refluxed for 18 hours
  3. distillationThe solvent is distilled off
  4. washthe residue is washed with water
  5. extractionextracted with dichloromethane
  6. customEvaporation of the solvent and crystallization of the residue from ethanol
  7. customgives 3.87 g

Sources & evidence

ORD record
ord-7eb89bf05afa4e17aa7912120d86889f
Source dataset
uspto-grants-1978_02
Patent number
US04075341

Reaction notes

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