Ethyl chloroacetate → 2H-BENZOTRIAZOLE-2-ACETIC ACID, ETHYL ESTER

HRID 2257812Notes

Reaction equation

HRID 2257812 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1)[CH3:22]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 10340Sodium CarbonateHCID 178418385HCID 178418385, compound

Product 1

HCID 8202342H-BENZOTRIAZOLE-2-ACETIC ACID, ETHYL ESTER

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

59.5 g benzotriazole (0.50 mol) was dissolved in 700 ml dimethylformamide. 160 g Sodium carbonate (1.5 mol) was added and then dropwise 73.5 g ethyl chloroacetate (0.60 mol). The stirred mixture was slowly heated to 40° C., and kept at that temperature for 17 h. The solvent was evaporated and the residue was extracted with ethyl acetate. GC showed one major and one minor product. The minor product ethyl-2-(2-benzotriazolyl)acetate was isolated by fractional crystallization from cold mixtures of ethanol and ethyl acetate.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate

Sources & evidence

ORD record
ord-20eaaa849e84471a99a2b3bdb9ffcf0e
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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