Ethyl orthoformate → 5-(Chloromethyl)-9-methyl-1,2,4-triazolo[4,3-c]quinazoline
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]=[C:8]([CH3:15])[CH:9]=2)[N:4]=1.[CH:16](OCC)(OCC)OCC>>[Cl:1][CH2:2][C:3]1[N:12]2[CH:16]=[N:14][N:13]=[C:11]2[C:10]2[CH:9]=[C:8]([CH3:15])[CH:7]=[CH:6][C:5]=2[N:4]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
4. 58.2 g of 2-(chloromethyl)-4-hydrazino-6-methylquinazoline in 870 ml of triethyl orthoformate are heated to reflux temperature while stirring in an oil bath pre-heated to 100° C. and stirred at this temperature for a further 0.5 h. (bath temperature 140°-145° C.). About 40 ml of ethanol are distilled off during the heating. Thereafter, the mixture is concentrated in a vacuum to a volume of about 150 ml. 150 ml of diethyl ether are then added thereto, the mixture is cooled to 0° to 5° C. and the crystals are filtered off. The product is washed with ethanol/diethyl ether 1:2 and with diethyl ether and dried in a vacuum. 55.1 g of crude 5-(chloro-methyl)-9-methyl-1,2,4-triazolo[4,3-c]quinazoline of m.p. 175° C. are obtained.
Workup
- temperatureto reflux temperature
- stirringstirred at this temperature for a further 0.5 h. (bath temperature 140°-145° C.)
- distillationAbout 40 ml of ethanol are distilled off during the heating
- concentrationThereafter, the mixture is concentrated in a vacuum to a volume of about 150 ml
- addition150 ml of diethyl ether are then added
- temperaturethe mixture is cooled to 0° to 5° C.
- filtrationthe crystals are filtered off
- washThe product is washed with ethanol/diethyl ether 1:2 and with diethyl ether
- customdried in a vacuum
Sources & evidence
- ORD record
- ord-2ab04f77446c4da49c2085019344ef82
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387585
Reaction notes
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