Triethylamine → 5-Methyl-3-(o-isothiocyanatobenzyl)-1,2,4-triazole

HRID 1982139Notes

Reaction equation

HRID 1982139 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]1[NH:10][N:9]=[C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[N:7]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:5][C:6]1[NH:10][N:9]=[C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]=[C:1]=[S:2])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 23317337HCID 23317337, compound

Product 1

HCID 233173365-Methyl-3-(o-isothiocyanatobenzyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.41 g of thiophosgene in 30 ml of methylene chloride is added dropwise at 0° a solution of 7.5 g of 5-methyl-3-(o-aminobenzyl)-1,2,4-triazole and 8.07 g of triethylamine in 285 ml of methylene chloride over a period of 45 minutes. The mixture is stirred at room temperature overnight, washed first with 10% aqueous potassium bicarbonate, then with water, dried over magnesium sulfate, decolorized with charcoal and evaporated to dryness to give 5-methyl-3-(o-isothiocyanatobenzyl)-1,2,4-triazole; IR 2080 cm-1.

Workup

  1. washwashed first with 10% aqueous potassium bicarbonate
  2. dry with materialwith water, dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3928a52f322148f293fc2bb5b26f5036
Source dataset
uspto-grants-1986_06
Patent number
US04595535

Reaction notes

Loading…