Sodium Hydroxide → 4-Bromo-2-(1H-1,2,4-triazol-3-yl)aniline

HRID 1786103Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8]C(=O)[N:6]3[N:13]=[CH:14][N:15]=[C:5]3[C:4]=2[CH:3]=1.[OH-].[Na+]>C(O)CO>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:8])=[C:4]([C:5]2[NH:6][N:13]=[CH:14][N:15]=2)[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a well stirred slurry of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100° C., was added aqeous NaOH (32%, 22.4 mL, 241 mmol). The slurry was heated at 140° C. for 17.5 h. The resulting solution was cooled to 27° C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 [M+H+].

Workup

temperatureThe resulting solution was cooled to 27° C.
customto crystallize
additionWater (146 mL) and 1-octanol (1.73 mL) were added
additionthe pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL)
filtrationthe solid was collected by filtration
washwashed with water and 2-propanol
customDrying in vacuo

Sources & evidence

ORD record: ord-f1676d3cb5184b028f71fce2467eb385
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507728B2

Reaction notes

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