Dimethyl Sulfoxide → Dioxolane,2(2,4-DiCLPh)-2-(1,2,4-triazolyl)methy

HRID 1758967Notes

Reaction equation

HRID 1758967 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.CS(C)=O.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH2:28]Br)[O:24][CH:23]([CH2:25][O:26][CH3:27])[CH2:22][O:21]1>O>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH2:28][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)[O:24][CH:23]([CH2:25][O:26][CH3:27])[CH2:22][O:21]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 15917766HCID 15917766, compound

Product 1

HCID 15917767Dioxolane,2(2,4-DiCLPh)-2-(1,2,4-triazolyl)methy

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 13 parts of powdered potassium hydroxide (85% purity), 15 parts of 1H-1,2,4-triazole and 165 parts of dimethylsulfoxide is heated at 80° C. for 1 hour. 58 Parts of 2-(2,4-dichlorophenyl)-2-(bromomethyl)-4-(methoxymethyl)-1,3-dioxolane are added and the whole is heated at 150° C. for 12 hours. The reaction mixture is poured onto 1000 parts of water. The product is extracted with 1,1'-oxybisethane. The extract is dried, filtered and evaporated. The residue is distilled under high vacuum yielding pure 1-[2-(2,4-dichlorophenyl)-4-(methoxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole; bp. 161°-168° C. at 0.01 mm. pressure. The product crystallizes on standing, yielding a solid having a melting point of 64°-74° C.

Workup

  1. temperaturethe whole is heated at 150° C. for 12 hours
  2. extractionThe product is extracted with 1,1'-oxybisethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-896ada2b9a4d494e8b9a686c1621b3e2
Source dataset
uspto-grants-1982_07
Patent number
US04338327

Reaction notes

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