Triethylamine → HCID 178517816, compound

HRID 1580438Notes

Reaction equation

HRID 1580438 reaction equation
[C:1]1([N:7]2[CH:11]=[N:10][C:9]([OH:12])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:20]Cl>CN(C)C=O>[C:1]1([N:7]2[C:11]([Cl:20])=[N:10][C:9]([OH:12])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24526ChlorineHCID 178517978HCID 178517978, compound

Product 1

HCID 178517816HCID 178517816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32.2 g of 1-phenyl-3-hydroxy-1,2,4-triazole and 40.5 g of triethylamine in 300 ml of dimethyl formamide. While cooling with ice, 21.3 g of chlorine gas are passed in at 20° to 30°C. Subsequently the resulting triethylamine hydrochloride is filtered off and the solvent is distilled off in vacuo. The residue is taken up in 300 ml of water and extracted 4 times with 200 ml of ether. The combined ethereal extracts are dried over sodium sulphate and, after the solvent has been filtered off, concentrated in vacuo. The residue is recrystallised from acetonitrile. Yield: 15.0 g (38.4 % of theory); m.p. 146°-147°C.

Workup

  1. customare passed in at 20° to 30°C
  2. filtrationSubsequently the resulting triethylamine hydrochloride is filtered off
  3. distillationthe solvent is distilled off in vacuo
  4. extractionextracted 4 times with 200 ml of ether
  5. dry with materialThe combined ethereal extracts are dried over sodium sulphate
  6. filtrationafter the solvent has been filtered off
  7. concentrationconcentrated in vacuo
  8. customThe residue is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-58f03176e51f45f2b2fc6b1d8cb23411
Source dataset
uspto-grants-1976_01
Patent number
US03932629

Reaction notes

Loading…