Sodium hydride → 5-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3-yl)-benzamide

HRID 926835Notes

Reaction equation

HRID 926835 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([NH2:14])[NH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>O1CCCC1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[C:24]([CH:28]=1)[C:25]([NH:14][C:11]1[NH:12][N:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:1])[F:16])[CH:4]=2)[N:10]=1)=[O:26]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27236855-Chloro-2-nitrobenzoyl chlorideHCID 178508289HCID 178508289, compound

Product 1

HCID 1785225335-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3-yl)-benzamideYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(3-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3-amine (100 mg, 0.44 mmol, 1.00 equiv) in tetrahydrofuran (1 mL) was added sodium hydride (35 mg, 0.88 mmol, 2.00 equiv, 60%) followed by the dropwise addition of a solution of 5-chloro-2-nitrobenzoyl chloride (96.49 mg, 0.44 mmol, 1.00 equiv) in tetrahydrofuran (1 mL) and the resulting solution was stirred for 2 h at room temperature. The mixture was diluted with 50 mL of ethyl acetate, washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 120 mg (67%) of a yellow solid.

Workup

  1. washwashed with 2×20 mL of brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d1dbdf3732274c33bfa095e4378cb360
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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