2-Bromo-1-(1-naphthalenyl)ethanone → 4-amino-1-[2-(1-naphthalenyl)-2-oxoethyl]-1H-1,2,4-triazolium bromide

HRID 581706Notes

Reaction equation

HRID 581706 reaction equation
[NH:1]1[CH2:5][N:4]([NH2:6])[CH:3]=[N:2]1.[Br:7][CH2:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10]>C(#N)C>[Br-:7].[NH2:6][N:4]1[CH2:5][NH+:1]([CH2:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])[N:2]=[CH:3]1

Participants

4

Reactant 2

HCID 38305132-Bromo-1-(1-naphthalenyl)ethanoneHCID 114803981H-1,2,4-triazol-4-amine

Product 1

HCID 212540014-amino-1-[2-(1-naphthalenyl)-2-oxoethyl]-1H-1,2,4-triazolium bromideYield 122%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1H-1,2,4-triazol-4-amine (44 g), 2-bromo-1-(1-naphthalenyl)ethanone (200 g) and acetonitrile (1000 ml) was stirred for 3 hours at reflux temperature. After cooling, the precipitated product was filtered off, washed with acetonitrile and dried in vacuo, yielding 209 g (78.4%) of 4-amino-1-[2-(1-naphthalenyl)-2-oxoethyl]-1 H-1,2,4-triazolium bromide; mp. 170° C. (interm. 7).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe precipitated product was filtered off
  4. washwashed with acetonitrile
  5. customdried in vacuo

Sources & evidence

ORD record
ord-086143ee920c4decafb6421849efeba0
Source dataset
uspto-grants-1999_07
Patent number
US05922718

Reaction notes

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