1H-1,2,4-Triazole → HCID 13391184, compound

HRID 1982406Notes

Reaction equation

HRID 1982406 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]2([CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH2:9][O:8]2)=[CH:5][CH:6]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[S:3][C:4]([C:7]([OH:8])([CH2:9][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 133911832-(5-Bromothiophen-2-yl)-2-[(4-chlorophenoxy)methyl]oxirane

Product 1

HCID 13391184HCID 13391184, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

16 g of crude 2-(2-bromo-thien-5-yl)-2-(4-chlorophenoxymethyl)-oxirane in 200 ml of acetonitrile are heated under reflux with 11 g (0.157 mol) of 1,2,4-triazole and 5 g of potassium carbonate for 4 hours. Thereafter, the reaction mixture is poured onto water, and extracted with methylene chloride. The methylene chloride phase is dried over sodium sulphate and evaporated down in vacuo. The residue is chromatographed over silica gel using the chloroform/ethyl acetate (1:1) system. 10.5 g (55% of theory) of 2-(2-bromo-thien-5-yl)-1-(4-chlorophenoxy)-3-(1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of a yellow resin which crystallizes after standing for a long time. Melting point 108°-112° C.

Workup

  1. additionThereafter, the reaction mixture is poured onto water
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride phase is dried over sodium sulphate
  4. customevaporated down in vacuo
  5. customThe residue is chromatographed over silica gel using the chloroform/ethyl acetate (1:1) system

Sources & evidence

ORD record
ord-d3b7ca87304c45949cb94bcb51f9a627
Source dataset
uspto-grants-1986_06
Patent number
US04596815

Reaction notes

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