1H-1,2,4-Triazole → 2-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide

HRID 1981601Notes

Reaction equation

HRID 1981601 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH2:14]Cl)[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>O1CCCC1>[Cl:1][CH2:2][C:3]([N:5]([CH2:14][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4]

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 130141982-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16.5 parts by weight of 2-chloro-2',6'-dimethyl-N-chloromethyl acetanilide and 9.3 parts by weight of 1,2,4-triazole are refluxed for 8 hours in 60 parts by volume of anhydrous tetrahydrofuran. After the mixture has been cooled, it is filtered, the filtrate is concentrated in vacuo, and the residue is dissolved in 60 parts by volume of chloroform, washed 3 times with water, each time with 40 parts by volume, and dried over sodium sulfate. After evaporation of the solvent in vacuo, there is isolated 21.0 parts by weight of 2-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, m.p.: 115°-118° C.; after recrystallization from ethanol, it melts at 120° C.

Workup

  1. temperatureAfter the mixture has been cooled
  2. filtrationit is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. dissolutionthe residue is dissolved in 60 parts by volume of chloroform
  5. washwashed 3 times with water
  6. dry with materialeach time with 40 parts by volume, and dried over sodium sulfate
  7. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-9d8613d64975456d8a66653c3a20dfcf
Source dataset
uspto-grants-1986_06
Patent number
US04593104

Reaction notes

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