Sodium Iodide → HCID 13186146, compound

HRID 2165119Notes

Reaction equation

HRID 2165119 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[N:10][CH:9]=[N:8]1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH2:27]Br)[O:25][CH:24]([CH3:26])[CH2:23][CH2:22][O:21]1.[I-].[Na+]>O.CS(C)=O>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH2:27][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[O:25][CH:24]([CH3:26])[CH2:23][CH2:22][O:21]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 23044288HCID 23044288, compound

Product 1

HCID 13186146HCID 13186146, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10.8 parts of potassium carbonate, 5.4 parts of 1H-1,2,4-triazole, 20.5 parts of 2-(2,4-dichlorophenyl)-2-(bromomethyl)-4-methyl-1,3-dioxane, 0.2 parts of sodium iodide and 100 parts of dimethylsulfoxide is stirred during 36 hours at 100° C., cooled and poured onto 600 parts of water. The reaction mixture is extracted three times with ethyl acetate and the combined organic layers are washed with 200 parts of water, dried, filtered and evaporated. The residual oil is purified by column-chromatography over silica gel using ethyl acetate as eluent. The pure fractions are collected and the eluent is evaporated, yielding 1-[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole; nD22 : 1.5505.

Workup

  1. temperaturecooled
  2. extractionThe reaction mixture is extracted three times with ethyl acetate
  3. washthe combined organic layers are washed with 200 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual oil is purified by column-chromatography over silica gel
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-4b86409f0cfa4df79aec109342a304f0
Source dataset
uspto-grants-1990_07
Patent number
US04939162

Reaction notes

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