2,4-Difluoronitrobenzene → N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

HRID 2426081Notes

Reaction equation

HRID 2426081 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([NH2:22])[CH3:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([NH:22][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH3:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 183341241-(3,5-Dichlorophenyl)ethanamine

Product 1

HCID 58707340N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamineYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-difluoro-nitrobenzene (3.13 mmol), 1-(3,5-dichlorophenyl)ethanamine (3.13 mmol) and N,N-diisopropylethylamine (6.3 mmol) were stirred at 45° C. in dry acetonitrile (25 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (11% yield). 1H NMR (400 MHz, CDCl3): δ 9.23 (s, 1H), 7.87 (t, 1H), 7.28 (s, 1H), 7.19 (s, 2H), 6.41 (t, 1H), 6.11 (d, 1H), 4.51 (m, 1H), 1.62 (d, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2bf916a235bb49958f668c5eaebe5d13
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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