Dimethyl acetylenedicarboxylate → HCID 21282595, compound

HRID 414091Notes

Reaction equation

HRID 414091 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[F:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH2:14][N:15]=[N+:16]=[N-:17].FC1C=CC=CC=1CN1C(C(N)=O)=C(C(N)=O)N=N1>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH2:14][N:15]1[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:1]([C:7]([O:9][CH3:10])=[O:8])[N:17]=[N:16]1

Participants

5

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 21282607HCID 21282607, compoundHCID 212826511-(Azidomethyl)-2-fluorobenzene

Product 1

HCID 21282595HCID 21282595, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

The starting material may also be prepared as follows: A solution of 40 g (0.282 mole) of dimethyl acetylenedicarboxylate in 500 ml of toluene is added dropwise to a solution of 41.5 g (0.255 mole) of o-fluorobenzyl azide in 50 ml of toluene, which solution has been heated to 90° C. After a further 5 hours at 90° C., the toluene is stripped off, the reaction mixture is cooled and the crystalline product is filtered with suction. Recrystallisation from a 1:1 mixture of diethyl ether/petroleum ether yields dimethyl 1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate with a melting point of 49°-51° C.

Workup

  1. customThe starting material may also be prepared
  2. temperaturethe reaction mixture is cooled
  3. filtrationthe crystalline product is filtered with suction
  4. customRecrystallisation
  5. additionfrom a 1:1 mixture of diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-5b948ebf87bd4c20bdc98bc3c06b9625
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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