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

HRID 1293120Notes

Reaction equation

HRID 1293120 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:19])[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N-:20]=[N+:21]=[N-:22].[Na+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[C:11]([C:12]1[NH:22][N:21]=[N:20][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19]

Participants

5

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 52.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution (3.0 mL) of ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate (104 mg, 0.39 mmol) in N,N-dimethylformamide was added to a solution (5.0 mL) of sodium azide (40 mg, 0.62 mmol) in N,N-dimethylformamide at 5° C. The temperature of the reaction solution was raised to room temperature before the reaction solution was stirred for 6 hr. After the completion of the reaction, iced water (10 mL) was added to the reaction solution, and the mixture was washed with ethyl acetate. The aqueous layer was then adjusted to pH 1.5 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 (63 mg, yield 52%).

Workup

  1. additionwas added to the reaction solution
  2. washthe mixture was washed with ethyl acetate
  3. additionThe aqueous layer was then adjusted to pH 1.5 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-fbb2aec1771c4e0caba76d53e61a8d00
Source dataset
uspto-grants-2007_07
Patent number
US07238719B2

Reaction notes

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