Chlorine → HCID 178456690, compound

HRID 1580436Notes

Reaction equation

HRID 1580436 reaction equation
[CH:1]([N:4]1[CH:8]=[N:7][C:6]([OH:9])=[N:5]1)([CH3:3])[CH3:2].[Cl:10]Cl>C(N(CC)CC)C>[CH:1]([N:4]1[C:8]([Cl:10])=[N:7][C:6]([OH:9])=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 178456444HCID 178456444, compound

Product 1

HCID 178456690HCID 178456690, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

127 g of 1-isopropyl-3-hydroxy-1,2,4-triazole and 276 ml of triethylamine are dissolved in 1200 ml of absolute alcohol. The solution turns cloudy yellow. While cooling (26° to 30°C), 106.5 g of chlorine (dried by concentrated sulphuric acid) are passed in within 30 minutes. In the process, the yellow solution initially becomes clear. Subsequently triethylamine hydrochloride precipitates as crystalline product, which is filtered off after stirring for 1 further hour. The filtrate is concentrated to dryness in a rotary evaporator. The brown residue is dissolved in 1 liter of water and 1 liter of ether. The mixture is extracted and separated in a separating funnel. The aqueous phase is extracted three times with 500 ml of ether on each occasion. The combined ether phases are dried over sodium sulphate, the drying agent is filtered off and the filtrate is concentrated to dryness. The light brown residue is dissolved in 500 ml of carbon tetrachloride containing activated charcoal, whereupon the mother liquor is concentrated to 1/3 of its volume and then cooled. The active substance crystallises out and is dried in vacuo for 15 hours at 60°C/15 mm Hg. Yield: 96.3 g (60 % of theory); m.p. : 103°-105°C.

Workup

  1. customare passed in within 30 minutes
  2. customSubsequently triethylamine hydrochloride precipitates as crystalline product, which
  3. filtrationis filtered off
  4. concentrationThe filtrate is concentrated to dryness in a rotary evaporator
  5. dissolutionThe brown residue is dissolved in 1 liter of water
  6. extractionThe mixture is extracted
  7. customseparated in a separating funnel
  8. extractionThe aqueous phase is extracted three times with 500 ml of ether on each occasion
  9. dry with materialThe combined ether phases are dried over sodium sulphate
  10. filtrationthe drying agent is filtered off
  11. concentrationthe filtrate is concentrated to dryness
  12. dissolutionThe light brown residue is dissolved in 500 ml of carbon tetrachloride containing activated charcoal, whereupon the mother liquor
  13. concentrationis concentrated to 1/3 of its volume
  14. temperaturecooled
  15. customThe active substance crystallises out and
  16. customis dried in vacuo for 15 hours at 60°C/15 mm Hg
  17. custom103°-105°C.

Sources & evidence

ORD record
ord-4732d8aa3619417c87fcac0aa2954c1e
Source dataset
uspto-grants-1976_01
Patent number
US03932629

Reaction notes

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