Dimethylamine → HCID 59202384, compound

HRID 1967650Notes

Reaction equation

HRID 1967650 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]=[CH:25][C:24](F)=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1.[CH3:32][NH:33][CH3:34].O>C(#N)C>[CH3:32][N:33]([CH3:34])[C:24]1[CH:25]=[CH:26][C:21]([C:20]([NH:19][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([C:8]([F:17])([C:13]([F:14])([F:16])[F:15])[C:9]([F:12])([F:10])[F:11])=[CH:5][C:4]=2[CH3:18])=[O:31])=[CH:22][C:23]=1[N+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 592023834-Fluoro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]-3-nitrobenzamide

Product 1

HCID 59202384HCID 59202384, compoundYield 100%

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]-4-fluoro-3-nitrobenzamide (5.0 g, 11 mmol) (prepared according to WO 05/073165) in acetonitrile (100 ml) was added a solution of N,N-dimethylamine in water (40% by weight) (3.55 ml, 28 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. Then the reaction mixture was concentrated and the residue purified by chromatography over silica gel (eluent: ethyl acetate) to give 4-dimethylamino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitrobenzamide (5.3 g, 100% yield).

Workup

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

Sources & evidence

ORD record
ord-0b23e3218c784d92840cf391c6cced43
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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