Water → Ethyl 4-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-5-carboxylate

HRID 1293116Notes

Reaction equation

HRID 1293116 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[O:23])[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].O>CN(C)C=O.[Cu]Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:15]([C:16]1[NH:3][N:2]=[N:1][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:23]

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 53400457Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate

Product 1

HCID 178470512Ethyl 4-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-5-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Copper(I) chloride (7.5 mg, 0.075 mmol) was added at room temperature to a solution (1.0 mL) of sodium azide (74 mg, 1.1 mmol) in N,N-dimethylformamide. A solution (1.5 mL) of ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenate (200 mg, 0.76 mmol) in N,N-dimethylformamide was added to this mixed solution at 5° C. The temperature of the reaction solution was raised to room temperature before the reaction solution was stirred for 8 hr. After the completion of the reaction, the reaction solution was poured into iced water, and the mixture was extracted with a saturated aqueous sodium hydrogencarbonate solution. The aqueous layer was adjusted to pH 1.8 by the addition of 2 N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then removed by evaporation under the reduced pressure. The oil thus obtained was dried in vacuo to give ethyl 5-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-4-carboxylate (149 mg, 65%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe mixture was extracted with a saturated aqueous sodium hydrogencarbonate solution
  3. additionThe aqueous layer was adjusted to pH 1.8 by the addition of 2 N hydrochloric acid
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was then removed by evaporation under the reduced pressure
  7. customThe oil thus obtained
  8. customwas dried in vacuo

Sources & evidence

ORD record
ord-9889bb24b6c64e219c87b525d58cb7ed
Source dataset
uspto-grants-2007_07
Patent number
US07238719B2

Reaction notes

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