Water → HCID 59202381, compound

HRID 1967649Notes

Reaction equation

HRID 1967649 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1F.[CH2:32]([NH2:34])[CH3:33].O>C(#N)C>[CH3:18][C:4]1[CH:5]=[C:6]([C:8]([F:17])([C:9]([F:11])([F:10])[F:12])[C:13]([F:16])([F:15])[F:14])[CH:7]=[C:2]([CH3:1])[C:3]=1[NH:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[NH:34][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 59202379HCID 59202379, compound

Product 1

HCID 59202381HCID 59202381, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluoro-5-nitrobenzamide (5.0 g, 11 mmol) (see Example I4) in acetonitrile (100 ml) was added a solution of N-ethylamine in water (70% by weight) (2.23 ml, 28 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was concentrated and the residue purified by chromatography over silica gel (eluent: ethyl acetate) to give N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-ethylamino-5-nitrobenzamide (4.8 g, 91% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography over silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-b1cf32da6aec4d2aa52cfa9f1a061859
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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