Water → HCID 178522598, compound

HRID 2263138Notes

Reaction equation

HRID 2263138 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.N1C=CC=CC=1.Cl[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15].O>O1CCCC1>[NH:1]1[CH:5]=[N:4][C:3]([NH:6][C:14](=[O:15])[O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 178418311HCID 178418311, compound

Product 1

HCID 178522598HCID 178522598, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-1,2,4-triazole-3-amine (1.00 g, 11.9 mmol) and pyridine (1.16 ml, 14.3 mmol) in tetrahydrofuran (40 ml) was added 2,2,2-trichloroethyl chloroformate (1.97 ml, 14.3 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the desired product (1.38 g, 44.5%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5964170a60674eb4bcfc16ce6fb42d23
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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