Acetic Anhydride → 5-(N-acetyl-N-methylamino)-3-(tert-butyl)-1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole

HRID 1650770Notes

Reaction equation

HRID 1650770 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([NH:10][CH3:11])[N:7]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O[C:25](=[O:27])[CH3:26])(=O)C>>[C:25]([N:10]([C:8]1[N:7]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:9]=1)[CH3:11])(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 146243803-(tert-butyl)-5-(N-methylamino)-1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole

Product 1

HCID 146243875-(N-acetyl-N-methylamino)-3-(tert-butyl)-1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazoleYield 73.2%

Procedure

6.7 g (0.02 mol) of 3-(tert-butyl)-5-(N-methylamino)-1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole was added to 51 g (0.5 mol) of acetic anhydride, and the mixture was stirred under reflux for 1 hour. Then, excess acetic anhydride was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5.5 g (yield: 73.3 g) of the desired compound as white powder. Melting point: 93°-94° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThen, excess acetic anhydride was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3cf8d90c4f87455f895d24a80e219708
Source dataset
uspto-grants-1990_05
Patent number
US04925864

Reaction notes

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