Ethyl orthoformate → N-diethoxymethyltriazole

HRID 567119Notes

Reaction equation

HRID 567119 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[CH:6](OCC)([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[CH2:8]([O:7][CH:6]([O:10][CH2:11][CH3:12])[N:1]1[CH:5]=[CH:4][N:3]=[N:2]1)[CH3:9]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 178418936HCID 178418936, compound

Product 1

HCID 22280793N-diethoxymethyltriazoleYield 56.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

After the addition of 2.5 g of p-toluenesulphonic acid hydrate, 34.5 g (0.5 mol) of triazole in 222 g (1.5 mol) of triethyl orthoforrnate are heated until the internal temperature reaches 150° C., while ethanol is distilled off. 2 g of sodium carbonate are added and the mixture is distilled using high vacuum. 48.6 g (56.8% of theory) of N-diethoxymethyltriazole are obtained.

Workup

  1. temperatureare heated until the internal temperature
  2. distillationis distilled off
  3. addition2 g of sodium carbonate are added
  4. distillationthe mixture is distilled

Sources & evidence

ORD record
ord-fe972614f61442adbbc6e82f0b3b88b3
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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