Bromine → HCID 19788770, compound

HRID 1656662Notes

Reaction equation

HRID 1656662 reaction equation
[CH2:1]([O:11][C:12]([CH:14]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:21])[N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].[Br:33]Br>C(Cl)(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([C:14]([N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)([C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:13])[Br:33])=[O:21])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 24408BromineHCID 19788761HCID 19788761, compound

Product 1

HCID 19788770HCID 19788770, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-[bis(isodecyloxycarbonyl)methyl]-1,2,4-triazole (51.8 g, 86% strength) was stirred and boiled under reflux at 78° with carbon tetrachloride (100 cm3) whilst bromine (16.0 g) was added slowly beneath the liquid surface during 30 minutes. Stirring and heating at 78°-80° was continued for a further period of 2 hours, the extent of bromination being followed by disappearance of the resonance due to the methine proton at delta=5.8 ppm from tetramethylsilane in the nmr spectrum. The solution was then cooled, washed with dilute aqueous sodium sulphite solution and with water, and the solvent was distilled yielding 57.2 g of 1-[1',1'-bis(isodecyloxycarbonyl)-1'-bromomethyl]-1,2,4-triazole of strength 76% as measured by non-aqueous titration with perchloric acid. This compound was evaluated as an extractant for copper using the procedure of Example 1 and the results are presented in Table 1.

Workup

  1. additionwas added slowly beneath the liquid surface during 30 minutes
  2. temperatureheating at 78°-80°
  3. temperatureThe solution was then cooled
  4. washwashed with dilute aqueous sodium sulphite solution and with water
  5. distillationthe solvent was distilled

Sources & evidence

ORD record
ord-b50127b8fbf14fd393ee18e143478ca9
Source dataset
uspto-grants-1993_10
Patent number
US05254695

Reaction notes

Loading…