Sodium Iodide → HCID 12831726, compound

HRID 1706963Notes

Reaction equation

HRID 1706963 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10]Cl)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:6]=1)=[O:4].[I-:27].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10][I:27])[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 12831725HCID 12831725, compound

Product 1

HCID 12831726HCID 12831726, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 51.6 g (0.132 mole) of 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester and 29.8 g (0.198 mole) of sodium iodide in 1000 ml of acetone is refluxed for 45 minutes. The reaction mixture is thereupon concentrated in vacuo. Water is added to the residue and extraction is performed twice with methylene chloride. The organic phase is washed once with diluted aqueous sodium bisulphate solution and twice with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo. The residue is triturated with ether, whereupon the reaction product crystallises out. After filtration under suction and drying in vacuo, there is obtained 1-(2-benzoyl-4-chlorophenyl)-5-(iodomethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester, m.p. 139°-142°.

Workup

  1. concentrationThe reaction mixture is thereupon concentrated in vacuo
  2. additionWater is added to the residue and extraction
  3. washThe organic phase is washed once with diluted aqueous sodium bisulphate solution and twice with saturated sodium chloride solution
  4. dry with materialit is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated with ether, whereupon the reaction product
  7. customcrystallises out
  8. filtrationAfter filtration under suction
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-0a14030719bf4d25b62919f4792ab4f0
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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