2-(3,4-Dimethoxyphenoxy)acetic acid → 1-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-(3,4-dimethoxyphenoxy)ethanone

HRID 710060Notes

Reaction equation

HRID 710060 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[O:15][CH2:16][C:17](O)=[O:18]>C(Cl)(Cl)Cl.S(Cl)(Cl)=O>[N:1]1([C:17](=[O:18])[CH2:16][O:15][C:14]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:12]([O:11][CH3:10])[CH:13]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 2

HCID 218358392-(3,4-Dimethoxyphenoxy)acetic acidHCID 178418385HCID 178418385, compound

Product 1

HCID 867067731-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-(3,4-dimethoxyphenoxy)ethanoneYield 109.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 1H-benzo[d][1,2,3]triazole (11.2 g) in CHCl3 (120 ml), thionyl chloride (1.7 ml) was added and after stirring at room temperature for 30 minutes, 2-(3,4-dimethoxyphenoxy)acetic acid (5.00 g) was added and the mixture was stirred at room temperature for 1.5 hours. The precipitate was filtered off and the filtrate was washed with an aqueous solution of 2 N NaOH; thereafter, the organic layer was dried (MgSO4), filtered and concentrated to give the titled compound (8.06 g, colorless solid.)

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. filtrationThe precipitate was filtered off
  3. washthe filtrate was washed with an aqueous solution of 2 N NaOH
  4. dry with materialthereafter, the organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3160b0f8570a4c3ca351621bededf526
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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