Water → HCID 14535821, compound

HRID 2082047Notes

Reaction equation

HRID 2082047 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[N:23]([CH2:27]Cl)[CH:24]=[N:25][N:26]=1.O>CN(C)C=O>[Cl:21][C:22]1[N:23]([CH2:27][O:14][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)[CH:24]=[N:25][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 14535820HCID 14535820, compound

Product 1

HCID 14535821HCID 14535821, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

5.6 g of p-phenoxyphenol and 4.2 g of potassium carbonate are heated for 1 hour at 70° C. in 50 ml of anhydrous dimethylformamide. Subsequently, 5.6 g of 2-chloro-1-chloromethyl-1,3,4-triazole is added and the mixture stirred for 6 hours at 70° C. and overnight at room temperature (about 20° C.). The mixture is then poured into 500 ml of water and extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated. The residue is purified by chromatography over silica gel using n-hexane/ethyl acetate (2:1) as eluant. There is obtained 2.8 g of 2-chloro-1-[(p-phenoxyphenoxy)-methyl]-1,3,4-triazole as an oil.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-a746c375596d4db08b95d086603e35f5
Source dataset
uspto-grants-1993_02
Patent number
US05187182

Reaction notes

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