Water → 3-(2-Bromoethoxy)-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole

HRID 617447Notes

Reaction equation

HRID 617447 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([OH:14])=[N:12][S:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23]Br.O>C(#N)C>[Br:21][CH2:22][CH2:23][O:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][S:11][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178519022HCID 178519022, compound

Product 1

HCID 4773243-(2-Bromoethoxy)-4-(2,6-dichlorophenyl)-1,2,5-thiadiazoleYield 148.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile, were mixed and stirred 0.49 g of 3-(2,6-dichlorophenyl)-4-hydroxy-1,2,5-thiadiazole, 0.3 g of potassium carbonate, and 1.9 g of 1,2-dibromoethane at 80° C. for one hour. After spontaneous cooling, the reaction mixture was poured into water, and was extracted with diethyl ether. The diethyl ether layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water successively,dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel chromatography to obtain 1.04 g of 3-(2-bromoethoxy)-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole.

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe diethyl ether layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water
  3. concentrationconcentrated
  4. customThe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1c00319ebc1a4492b9b115905287df2d
Source dataset
uspto-grants-1999_09
Patent number
US05948916

Reaction notes

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