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

HRID 2066405Notes

Reaction equation

HRID 2066405 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-b80b6a55267c4d128bd4fbc4e17a78b7
Source dataset
uspto-grants-2012_10
Patent number
US08293730B2

Reaction notes

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