Iodoethane → L 11204

HRID 1733131Notes

Reaction equation

HRID 1733131 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-002d50ccb2624136b497e578878b5b7b
Source dataset
uspto-grants-1980_12
Patent number
USRE030456

Reaction notes

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