Thionyl Chloride → 2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl chloride

HRID 659932Notes

Reaction equation

HRID 659932 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:22])=O>ClCCCl.CN(C=O)C>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:22])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 574372702,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoic acid

Product 1

HCID 574372552,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl chlorideYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoic acid (0.46 g) and thionyl chloride (0.36 g) were added in 1,2-dichloroethane (10 ml), two drops of DMF were added and the mixture was refluxed by heating for 3 hours. After cooling, the solvent was distilled off to obtain the desired 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoyl chloride (0.49 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 3 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-59b7f4b5e21b46cea63560e22aade3c5
Source dataset
uspto-grants-2011_12
Patent number
US08084398B2

Reaction notes

Loading…