Pyridine → 5-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)pyrazin-2-yl)-benzamide

HRID 926773Notes

Reaction equation

HRID 926773 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([N+:34]([O-:36])=[O:35])=[C:29]([CH:33]=1)[C:30](Cl)=[O:31]>ClCCl>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([N+:34]([O-:36])=[O:35])=[C:29]([CH:33]=1)[C:30]([NH:15][C:12]1[CH:11]=[N:10][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=2)=[CH:14][N:13]=1)=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27236855-Chloro-2-nitrobenzoyl chlorideHCID 205670725-[3-(Trifluoromethyl)phenyl]pyrazin-2-amine

Product 1

HCID 665869555-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)pyrazin-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 5-(3-(trifluoromethyl)phenyl)pyrazin-2-amine (1.3 g, 5.43 mmol, 1.00 equiv) in dichloromethane (15 mL), and pyridine (2 mL). This was followed by dropwise addition of a solution of 5-chloro-2-nitrobenzoyl chloride (1.2 g, 5.45 mmol, 1.00 equiv) in dichloromethane (5 mL) with stirring. The resulting solution was stirred for 2 h at 25° C. in an oil bath. The resulting solution was diluted with 100 mL of dichloromethane. The resulting mixture was washed with 2×50 mL of hydrogen chloride (aq), dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in 2 g (87%) of 5-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)pyrazin-2-yl)benzamide as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 2 h at 25° C. in an oil bath
  3. washThe resulting mixture was washed with 2×50 mL of hydrogen chloride (aq)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 2 g (87%) of 5-chloro-2-nitro-N-(5-(3-(trifluoromethyl)phenyl)pyrazin-2-yl)benzamide as a yellow solid

Sources & evidence

ORD record
ord-7d3f612d0e00408597fcf1f5fb4eeeac
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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