Triethylamine → HCID 178448760, compound

HRID 1580440Notes

Reaction equation

HRID 1580440 reaction equation
[CH2:1]([N:5]1[CH:9]=[N:8][C:7]([OH:10])=[N:6]1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:18]Cl>C(O)C>[CH2:1]([N:5]1[C:9]([Cl:18])=[N:8][C:7]([OH:10])=[N:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24526ChlorineHCID 178448641HCID 178448641, compound

Product 1

HCID 178448760HCID 178448760, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

241 g of 1-isobutyl-3-hydroxy-1,2,4-triazole and 475 ml of triethylamine are dissolved in 2100 ml of absolute ethanol, and 182 g of chlorine are passed in while cooling at 20°-30°C. The solution is stirred for 1 1/4 hours at room temperature, after which the triethylamine hydrochloride is filtered off. The filtrate is concentrated in a rotary evaporator, the residue dissolved in 1000 ml of ether and 1000 ml of water are added. The phases are separated and the aqueous phase is extracted 3 times with 300 ml of ether each time. The ether phase is dried and concentrated. The residue is recrystallised from ligroin/xylene. Yield: 104.7 g (34 % of theory); m.p. 84°-86°C.

Workup

  1. temperaturewhile cooling at 20°-30°C
  2. filtrationafter which the triethylamine hydrochloride is filtered off
  3. concentrationThe filtrate is concentrated in a rotary evaporator
  4. dissolutionthe residue dissolved in 1000 ml of ether
  5. addition1000 ml of water are added
  6. customThe phases are separated
  7. extractionthe aqueous phase is extracted 3 times with 300 ml of ether each time
  8. dry with materialThe ether phase is dried
  9. concentrationconcentrated
  10. customThe residue is recrystallised from ligroin/xylene

Sources & evidence

ORD record
ord-f03db375478b44fab0a4555b27a89ba0
Source dataset
uspto-grants-1976_01
Patent number
US03932629

Reaction notes

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