Iodine chloride → 1-(4-Amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole

HRID 2231659Notes

Reaction equation

HRID 2231659 reaction equation
[I:1]Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:6][C:5]=1[CH3:15].C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:3][C:4]1[C:5]([CH3:15])=[CH:6][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:8][C:9]=1[I:1]

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 144502622-Methyl-4-[1,2,4]triazol-1-yl-phenylamine

Product 1

HCID 212855261-(4-Amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (5.103 g) was added dropwise to a stirred solution of 1-(4-amino-3-methylphenyl)-1,2,4-triazole (5.22 g) and sodium acetate (2.583 g) in acetic acid (100 cm3). After 16 hours volatile material was removed in vacuo and the residue was partitioned between dichloromethane (100 cm3) and sodium carbonate solution (50 cm3). The organic phase was washed with sodium thiosulphate solution (10 g in 50 cm3 water), dried (MgSO4) and evaporated to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate. Combination and evaporaton of the appropriate fractions gave a solid which was recrystallised from ethyl acetate-ether to afford the title compound, m.p. 151°-154° (3.1 g).

Workup

  1. customAfter 16 hours volatile material was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (100 cm3) and sodium carbonate solution (50 cm3)
  3. washThe organic phase was washed with sodium thiosulphate solution (10 g in 50 cm3 water)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a solid which
  7. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with ethyl acetate
  9. customCombination and evaporaton of the appropriate fractions gave a solid which
  10. customwas recrystallised from ethyl acetate-ether

Sources & evidence

ORD record
ord-1f8d4b16703e4cd78f7cef02a21f161b
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

Loading…