Water → 9-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one

HRID 1786102Notes

Reaction equation

HRID 1786102 reaction equation
C(O[C:4](=[O:15])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[C:13]#[N:14])C.[CH:16]([NH:18]N)=O.O.C[N:22]1C(=O)CCC1>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:4](=[O:15])[N:14]3[N:22]=[CH:16][N:18]=[C:13]3[C:7]=2[CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 12229HydrazinecarboxaldehydeHCID 13387N-methyl-2-pyrrolidoneHCID 18367857Ethyl (4-bromo-2-cyanophenyl)carbamate

Product 1

HCID 1357668559-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-oneYield 81%

Conditions

Temperature
160 °C

Procedure

To a solution of (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25° C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81%) as a light yellow solid. MS: m/e 264.9/267.0 [M+H+].

Workup

  1. temperatureIt was cooled to below 100° C.
  2. temperatureThe resulting slurry was cooled to 25° C.
  3. stirringstirred for 15 min
  4. filtrationThe solid was collected by filtration
  5. washwashed with water and 2-propanol
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-271bca5206bf4b1ca62ec2973902481e
Source dataset
uspto-grants-2009_03
Patent number
US07507728B2

Reaction notes

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