Water → 4-(2,6-Dichlorophenyl)-1,2,5-thiadiazol-3-yl acetate

HRID 1440191Notes

Reaction equation

HRID 1440191 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.N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].O>CCOCC>[C:21]([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)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178519022HCID 178519022, compound

Product 1

HCID 194291224-(2,6-Dichlorophenyl)-1,2,5-thiadiazol-3-yl acetateYield 70.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In ether, 0.5 g of 3-(2,6-dichlorophenyl)-4-hydroxy-1,2,5-thiadiazole and 0.18 g of pyridine were dissolved and 0.23 g of acetic anhydride was added thereto. The mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with ether. The ether layer was washed twice with aqueous dilute sodium hydroxide solution, twice with water and twice with aqueous saturated sodium chloride solution. The resultant was dried over anhydrous sodium sulfate and concentrated, followed by silica gel column chromatography to obtain 0.41 g of 4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-yl acetate.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed twice with aqueous dilute sodium hydroxide solution, twice with water and twice with aqueous saturated sodium chloride solution
  3. dry with materialThe resultant was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-176c71a6a6f543be98d800ffb608a4c5
Source dataset
uspto-grants-1996_03
Patent number
US05498593

Reaction notes

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