Sodium Hydroxide → 9-Trifluoromethoxy-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one

HRID 2241871Notes

Reaction equation

HRID 2241871 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1[C:17]1[NH:18][N:19]=[CH:20][N:21]=1)=[O:4].[OH-].[Na+].[Cl-].[NH4+]>O1CCOCC1>[F:14][C:13]([F:16])([F:15])[O:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:18]3[C:17](=[N:21][CH:20]=[N:19]3)[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 686936732-Chloro-N-[2-(2H-[1,2,4]triazol-3-yl)-4-trifluoromethoxy-phenyl]-acetamide

Product 1

HCID 1363351829-Trifluoromethoxy-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-oneYield 24.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-N-[2-(2H-[1,2,4]triazol-3-yl)-4-trifluoromethoxy-phenyl]-acetamide (3.15 g, 9.82 mmol) in dioxane (100 mL) was added aqueous sodium hydroxide (32%, 2.18 mL, 23.6 mmol) and the reaction mixture was stirred for 19 h at ambient temperature. It was poured onto aqueous ammonium chloride (1M, 50 mL) and the organic solvent was removed by destillation. The resulting suspension was filtered and the solid was washed with ice-cold water (50 mL). Drying in vacuo afforded the title compound (682 mg, 24%) as a light yellow solid. MS: m/e=285.0 [M+H]+.

Workup

  1. customthe organic solvent was removed by destillation
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with ice-cold water (50 mL)
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-15ef0c7686464e3cac77fadca1cd90fa
Source dataset
uspto-grants-2010_03
Patent number
US07671048B2

Reaction notes

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