Dimethyl acetylenedicarboxylate → 1-(o-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester

HRID 414085Notes

Reaction equation

HRID 414085 reaction equation
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH2:14][N:15]=[N+:16]=[N-:17]>C1C=CC=CC=1.C1CCCCC1>[CH3:1][O:2][C:3]([C:5]1[N:17]=[N:16][N:15]([CH2:14][C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[Cl:11])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 121946022-Chlorobenzyl azide

Product 1

HCID 146120651-(o-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8078CyclohexaneSolvent

Procedure

A solution of 8 g (0.054 mol) of acetylene-dicarboxylic acid dimethyl ester in 25 ml of benzene is added dropwise to a solution of 8.4 g (0.05 mol) of o-chlorobenzyl azide in 50 ml of benzene that is boiling under reflux. After a further hour under reflux, the whole is diluted with 75 ml of cyclohexane and, after cooling, the substance that has crystallised out is filtered off with suction. After washing with a mixture of diethyl ether and hexane (1:1), there is obtained 1-(o-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester having a melting point of 88°-91°.

Workup

  1. temperatureunder reflux
  2. temperatureAfter a further hour under reflux
  3. temperatureafter cooling
  4. customthe substance that has crystallised out
  5. filtrationis filtered off with suction
  6. washAfter washing with a mixture of diethyl ether and hexane (1:1)

Sources & evidence

ORD record
ord-8c6d185ec0a0483c9989fbe3a734f573
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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