Potassium Carbonate → 2-(Benzotriazol-1-ylmethoxy)-5-chloro-benzaldehyde

HRID 1929080Notes

Reaction equation

HRID 1929080 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[CH2:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:13]1([CH2:12][O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 33282221-(Chloromethyl)-1H-benzotriazole

Product 1

HCID 50961702-(Benzotriazol-1-ylmethoxy)-5-chloro-benzaldehydeYield 25.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

5-Chloro-2-hydroxy-benzaldehyde (8.45 g, 54 mmol) is dissolved in DMF (100 ml) and after addition of 1-(chlormethyl)-1H-benzotriazole (9.96 g, 59.4 mmol) and K2CO3 (9.7 g, 70.2 mmol) the mixture is stirred at 45° C. for 1 h (TLC control). Then the mixture is evaporated under high vacuum. The residue is diluted with ethyl acetate, washed with brine and dried over Na2SO4. Evaporation gave 3.9 g of a colorless solid. The product is used in the next step without further purification.

Workup

  1. customThen the mixture is evaporated under high vacuum
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-8660f87f1c014986be31c26fdd133559
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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