2-(Chloromethyl)-4-hydrazinylquinazoline → 5-(Chloromethyl)[1,2,4]triazolo[4,3-c]quinazoline

HRID 273775Notes

Reaction equation

HRID 273775 reaction equation
[Cl:1][CH2:2][C:3]1[N:12]=[C:11]([NH:13][NH2:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH:15]([O-])([O-])OCC>>[Cl:1][CH2:2][C:3]1[N:12]2[CH:15]=[N:14][N:13]=[C:11]2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 200940022-(Chloromethyl)-4-hydrazinylquinazolineHCID 53630039Ethylorthoformate

Product 1

HCID 200940255-(Chloromethyl)[1,2,4]triazolo[4,3-c]quinazoline

Conditions

Temperature
125 °C

Procedure

3.1. 88 g of 2-(chloromethyl)-4-hydrazinoquinazoline are suspended in 1.2 l of ethyl orthoformate. The suspension is heated (bath temp. 125° C.) while stirring and the resulting ethanol is distilled off. After 1 h., the mixture is cooled to 15° C., the precipitate is filtered off and washed with 100 ml of diethyl ether. The product is dried in a vacuum. 80 g of crude 5-(chloromethyl)-1,2,4-triazolo [4,3-c]quinazoline are obtained. The filtrate is concentrated in a vacuum and the residue is boiled in 20 ml of ethanol. The mixture is cooled to 0° C., filtered, the filter cake is washed with diethyl ether and the crystals are dried in a vacuum. A second portion of 5.3 g of crude 5-(chloromethyl)-1,2,4-triazolo[4,3-c]quinazoline is obtained. The two crude crystallizates (together 85.3 g) are stirred in 8.5 ml of dioxan at 85° C. for 1 h. The insoluble constituent is filtered off and the filtrate is concentrated to about 300 ml in a vacuum. The suspension is cooled, filtered and the filter cake is washed with 100 ml of diethyl ether. 66 g of 5-(chloromethyl)-1,2,4-triazolo [4,3-c]quinazoline of m.p. 189° C. (dec.) are obtained. A second portion of 2.5 g of 5-(chloromethyl)-1,2,4-triazolo[4,3-c]quinazoline is obtained after concentration of the filtrate.

Workup

  1. distillationthe resulting ethanol is distilled off
  2. temperaturethe mixture is cooled to 15° C.
  3. filtrationthe precipitate is filtered off
  4. washwashed with 100 ml of diethyl ether
  5. customThe product is dried in a vacuum

Sources & evidence

ORD record
ord-f21ef87eaad54d43ab45c7adcaf04f26
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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