Sodium hydride → 3-(4-Methoxypyrazol-1-yl)-7-chloro-benzo-1,2,4-triazine 1-oxide

HRID 1732878Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[N:7][NH:8][CH:9]=1.Cl[C:11]1[N:12]=[N+:13]([O-:22])[C:14]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:15]=2[N:16]=1>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[N:7][N:8]([C:11]2[N:12]=[N+:13]([O-:22])[C:14]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3.45 g (0.115 mol) of sodium hydride (80% pure) were introduced into a solution of 12.6 g (0.13 mol) of 4-methoxy-pyrazole in 100 ml of absolute dimethylformamide at room temperature and the mixture was subsequently warmed briefly to 60° C. 21.6 g (0.1 mol) of 3,7-dichloro-benzo-1,2,4-triazine 1-oxide were added in portions to the mixture, which had been cooled to room temperature. After the exothermic reaction had subsided, the mixture was subsequently stirred at 30° to 40° C. for a further 3 hours and the reaction product was then precipitated with water. This product was filtered off, stirred in 150 ml of methanol, filtered off again and dried. 17.3 g of 3-(4-methoxypyrazol-1-yl)-7-chloro-benzo-1,2,4-triazine 1-oxide of melting point 253°-255° C. (with decomposition) were obtained, that is to say 62.3% of theory. The compound could be recrystallized from dimethylformamide.

Workup

temperaturehad been cooled to room temperature
customAfter the exothermic reaction
customthe reaction product was then precipitated with water
filtrationThis product was filtered off
stirringstirred in 150 ml of methanol
filtrationfiltered off again
customdried

Sources & evidence

ORD record: ord-2b08ae69a0b04eccab9101c0214fe008
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239760

Reaction notes

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