Methanol → 3-(1-ethoxycarbonylpentoxy)-1-phenyl-1,2,4-1H-triazole

HRID 2106577Notes

Reaction equation

HRID 2106577 reaction equation
[Na].CO.[OH:4][C:5]1[N:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1.Br[CH:17]([CH2:23][CH2:24][CH2:25][CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CS(C)=O>[CH2:21]([O:20][C:18]([CH:17]([O:4][C:5]1[N:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1)[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 79072Ethyl 2-bromohexanoateHCID 5360545SodiumHCID 178517978HCID 178517978, compound

Product 1

HCID 150162523-(1-ethoxycarbonylpentoxy)-1-phenyl-1,2,4-1H-triazoleYield 27.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The process was carried out as shown in Example 7 above, beginning with 1.4 g of sodium, 30 ml of methanol, 150 ml of dimethylsulfoxide, 10 g of 3-hydroxy-1-phenyl-1,2,4-1H-triazole and 13.8 g of ethyl 2-bromohexanoate. The product was distilled at 205° and 1 mm of mercury to obtain 5.2 g of the desired product, an oil.

Workup

  1. distillationThe product was distilled at 205°

Sources & evidence

ORD record
ord-ead8a7bf3c5447a3a02cd77f33518811
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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