Potassium Carbonate → N-[2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylphenyl]-2-methoxy-3-nitrobenzamide

HRID 570757Notes

Reaction equation

HRID 570757 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:21])([C:17]([F:20])([F:19])[F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:6]=[C:5]([CH3:22])[C:4]=1[NH:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[C:26]=1F)[CH3:2].[C:36](=O)([O-])[O-:37].[K+].[K+]>CO>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:21])([C:17]([F:20])([F:19])[F:18])[C:10]([F:16])([F:15])[C:11]([F:12])([F:13])[F:14])[CH:6]=[C:5]([CH3:22])[C:4]=1[NH:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[C:26]=1[O:37][CH3:36])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86673887N-[2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylphenyl]-2-fluoro-3-nitrobenzamide

Product 1

HCID 86673889N-[2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylphenyl]-2-methoxy-3-nitrobenzamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-[2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylphenyl]-2-fluoro-3-nitrobenzamide (Example 12) (5 g, 9.6 mmol) in methanol (195 ml) was added potassium carbonate (2.6 g, 16.2 mmol) at ambient temperature. The reaction mixture was stirred for 16 hours at ambient temperature. The reaction mixture was concentrated and the residue was dissolved in dichloromethane. The organic phase was washed with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give N-[2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylphenyl]-2-methoxy-3-nitrobenzamide (5.1 g, 99% yield). 1H NMR (400 MHz, CDCl3): 8.90 (bs, 1H), 8.32 (d, 1H), 7.97 (d, 1H), 7.38 (m, 3H), 4.19 (s, 3H), 2.70 (q, 2H), 2.24 (s, 3H), 1.20 (t, 3H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-45d490b73a804304b9c34108b106d669
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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